Material for organic electroluminescence device and organic electroluminescence device using the same

ABSTRACT

Provided are an organic electroluminescence device, which shows high luminous efficiency, is free of any pixel defect, and has a long lifetime, and a material for an organic electroluminescence device for realizing the device. The material for an organic electroluminescence device is a compound having a π-conjugated heteroacene skeleton crosslinked with a carbon atom, nitrogen atom, oxygen atom, or sulfur atom. The organic electroluminescence device has one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one layer of the organic thin film layers contains the material for an organic electroluminescence device.

TECHNICAL FIELD

The present invention relates to a material for an organicelectroluminescence device and an organic electroluminescence deviceusing the material, in particular, an organic electroluminescencedevice, which shows high luminous efficiency, is free of any pixeldefect, and has a long lifetime, and a material for an organicelectroluminescence device for realizing the device.

BACKGROUND ART

An organic electroluminescence device (hereinafter,“electroluminescence” may be abbreviated as “EL”) is a spontaneous lightemitting device which utilizes the principle that a fluorescentsubstance emits light by energy of recombination of holes injected froman anode and electrons injected from a cathode when an electric field isapplied. Since an organic EL device of the laminate type driven under alow electric voltage was reported, many studies have been conducted onorganic EL devices using organic materials as the constituent materials.The devices of the laminate type use tris(8-quinolinolato) aluminum fora light emitting layer and a triphenyldiamine derivative for a holetransporting layer. Advantages of the laminate structure are that theefficiency of hole injection into the light emitting layer can beincreased, that the efficiency of forming exciton which are formed byblocking and recombining electrons injected from the cathode can beincreased, and that exciton formed within the light emitting layer canbe enclosed. As described above, for the structure of the organic ELdevice, a two-layered structure having a hole transporting (injecting)layer and an electron transporting light emitting layer and athree-layered structure having a hole transporting (injecting) layer, alight emitting layer, and an electron transporting (injecting) layer arewell known. To increase the efficiency of recombination of injectedholes and electrons in the devices of the laminate type, the structureof the device and the process for forming the device have been studied.

As the light emitting material of the organic EL device, chelatecomplexes such as tris(8-quinolinolato) aluminum complexes, coumarinederivatives, tetraphenylbutadiene derivatives, distyrylarylenederivatives, and oxadiazole derivatives are known. It is reported thatlight in the visible region ranging from blue light to red light can beobtained by using these light emitting materials, and development of adevice exhibiting color images is expected.

In addition, it has been recently proposed that a phosphorescentmaterial as well as a fluorescent material be utilized in the lightemitting layer of an organic EL device. High luminous efficiency isachieved by utilizing the singlet and triplet states of an excited stateof an organic phosphorescent material in the light emitting layer of anorganic EL device. Upon recombination of an electron and a hole in anorganic EL device, singlet excitons and triplet excitons may be producedat a ratio of 1:3 owing to a difference in spin multiplicity between thesinglet and triplet excitons, so the use of a phosphorescent materialmay achieve luminous efficiency three to four times as high as that of adevice using fluorescence alone.

Patent Documents 1 to 7 are exemplary inventions each describing suchmaterials for an organic EL device.

Patent Document 1 describes a compound using, as a mother skeleton, astructure obtained by crosslinking a terphenylene skeleton with, forexample, a carbon atom, nitrogen atom, or oxygen atom. The document,which mainly discloses data indicative of the potential of the compoundto serve as a hole transporting material, describes that the compound isused as a host material for a phosphorescent material in a lightemitting layer. However, the description is limited to a redphosphorescent device, and the luminous efficiency of the device is nothigh enough for the device to be put into practical use.

Patent Document 2 describes an indolocarbazole compound having asubstituent on a nitrogen atom or on an aromatic ring. The documentrecommends that the compound be used as a hole transporting material,and describes that a thermally and morphologically stable, thin holetransporting layer can be prepared from the compound. However, thedocument does not describe data indicative of the usefulness of thecompound as a host material or electron transporting material to be usedtogether with a phosphorescent material.

Patent Document 3 describes indolocarbazole compounds each having asubstituent on a nitrogen atom or on an aromatic ring. The documentdiscloses data on a green light emitting device using any one of thosecompounds as a host material for a phosphorescent material in its lightemitting layer. However, a high voltage must be applied to the device todrive the device, and the device shows low luminous efficiency, so thedevice cannot be sufficiently put into practical use.

Patent Document 4 describes indolocarbazole compounds each having asubstituent. The document describes that each of the compounds functionsas a host material for a phosphorescent material in a light emittinglayer. However, each of those compounds is characterized in that thecompound has a dimer or trimer structure through a linking group, andeach of the compounds tends to have a large molecular weight. Thedocument discloses data on a green phosphorescent device using any oneof those compounds, but all the compounds used each have a largemolecular weight of 800 or more. The efficiency with which a materialhaving a large molecular weight is deposited in a vacuum is poor, andthe material may decompose owing to heating for a long time period, sothe material may be insufficient in terms of practical use.

Patent Documents 5 and 6 describe indenofluorene compounds each having asubstituent on an aromatic ring, and describe that each of the compoundsfunctions as a fluorescent material in a light emitting layer. However,none of the documents describes data indicative of the usefulness ofeach of the compounds as a host material or electron transportingmaterial to be used together with a phosphorescent material.

Patent Document 7 describes compounds each using, as a mother skeleton,a structure obtained by crosslinking a terphenylene skeleton with asulfur atom, boron atom, or phosphorus atom. The document describes thateach of those compounds has excellent oxidation resistance, and allowsthe formation of an organic semiconductor active layer by an applicationmethod. However, the document does not describe data indicative of theusefulness of each of the compounds as a host material or electrontransporting material to be used together with a fluorescent material orphosphorescent material.

-   Patent Document 1: WO 2006/122630-   Patent Document 2: EP 0909787-   Patent Document 3: WO 2007/063796-   Patent Document 4: WO 2007/063754-   Patent Document 5: US 2002/0132134-   Patent Document 6: US 2003/0044646-   Patent Document 7: JP 2008-81494

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

The present invention has been made with a view to solving the aboveproblems, and an object of the present invention is to provide anorganic EL device which shows high luminous efficiency, is free of anypixel defect, and has a long lifetime, and a material for an organic ELdevice for realizing the device.

Means for Solving the Problems

The inventors of the present invention have made extensive studies witha view to achieving the above object. As a result, the inventors havefound that the above object can be achieved by using a compound having aπ-conjugated heteroacene skeleton crosslinked with a carbon atom,nitrogen atom, oxygen atom, or sulfur atom as a material for an organicEL device. Thus, the inventors have completed the present invention.

That is, the present invention provides a material for an organic ELdevice represented by the following formulae (1) or (2).

[In the formulae (1) and (2), Ar₁, Ar₂, and Ar₃ each independentlyrepresent a substituted or unsubstituted aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms or a substituted orunsubstituted aromatic heterocyclic group having a ring formed of 3 to24 atoms, provided that, Ar₁, Ar₂, and Ar₃ each may have one substituentY or multiple substituents Ys, in the case of multiple substituents Ys,the substituent Ys may be different from each other, Y represents analkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withAr₁, Ar₂, or Ar₃ through a carbon-carbon bond.

In the formulae (1) and (2), X₁, X₂, X₃, and X₄ each independentlyrepresent O, S, N—R₁ or CR₂R₃ (N atom of N—R, or C atom of CR₂R₃ bindsto Ar₁, Ar₂, or Ar₃).

In the formulae (1) and (2), R₁, R₂, and R₃ each independently representan alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₁ and X₂ representN—R₃, o and p each represent 0, and q represents 1, or when both X₁ andX₃ represent N—R₁, p and q each represent 0, and o represents 1, atleast one R₁ represents a substituted or unsubstituted, monovalent fusedaromatic heterocyclic group having a ring formed of 8 to 24 atoms.

In the formulae (1) and (2), o, p, and q each represent 0 or 1 and srepresents 1, 2, or 3. n represents 2, 3, or 4, and the materialrepresented by the formula (2) includes a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4.

In the formulae (1) and (2), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with Ar₁ through a carbon-carbon bond.

In the formula (1), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with Ar₃ through a carbon-carbon bond, provided that, when bothX₁ and X₂ represent CR₂R₃, o and p each represent 0, q represents 1, andboth L₁ and L₂ represent substituted or unsubstituted, monovalent ordivalent aromatic hydrocarbon groups each having a ring formed of 6 to24 carbon atoms, or when both X₁ and X₃ represent CR₂R₃, p and q eachrepresent 0, o represents 1, and both L₁ and L₂ represent substituted orunsubstituted, monovalent or divalent aromatic hydrocarbon groups eachhaving a ring formed of 6 to 24 carbon atoms, a case where L₁ and L₂ aresimultaneously linked at para positions with respect to Ar₂ is excluded.

In the formula (2), when n represents 2, L₃ represents a single bond, analkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with Ar₃ through a carbon-carbon bond, when nrepresents 3, L₃ represents a trivalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, trivalent cycloalkane having aring formed of 3 to 20 carbon atoms, a trivalent silyl group having 1 to20 carbon atoms, a substituted or unsubstituted, trivalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, trivalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with Ar₃through a carbon-carbon bond, or when n represents 4, L₃ represents atetravalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, tetravalent cycloalkane having a ring formed of 3 to 20carbon atoms, a silicon atom, a substituted or unsubstituted,tetravalent aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted, tetravalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with Ar₃ through a carbon-carbon bond, provided that, when bothX₁ and X₂ represent CR₂R₃, o and p each represent 0, q represents 1, andboth L₁ and L₂ represent substituted or unsubstituted, monovalent,divalent, trivalent, or tetravalent aromatic hydrocarbon groups eachhaving a ring formed of 6 to 24 carbon atoms, or when both X₁ and X₃represent CR₂R₃, p and q each represent 0, o represents 1, and both L₁and L₃ represent substituted or unsubstituted, monovalent, divalent,trivalent, or tetravalent aromatic hydrocarbon groups each having a ringformed of 6 to 24 carbon atoms, a case where L₁ and L₃ aresimultaneously linked at para positions with respect to Ar₂ is excluded.

In the formulae (1) and (2), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstitutedaromatic heterocyclic group which has a ring formed of 3 to 24 atoms andwhich is linked with L₁ through a carbon-carbon bond, provided that,when L₁ represents an alkyl or alkylene group having 1 to 20 carbonatoms, a case where A₁ represents a hydrogen atom is excluded.

In the formula (1), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withL₂ through a carbon-carbon bond, provided that, when L₂ represents analkyl or alkylene group having 1 to 20 carbon atoms, a case where A₂represents a hydrogen atom is excluded, and, when X₁ and X₂ eachrepresent O, S, or CR₂R₃, o and p each represent 0, q represents 1, andboth L₁ and L₂ represent single bonds, or when both X₁ and X₃ eachrepresent O, S, or CR₂R₃, p and q each represent 0, o represents 1, andboth L₁ and L₂ represent single bonds, a case where A₁ and A₂simultaneously represent hydrogen atoms is excluded; In the formulae (1)and (2), A₁, A₂, L₁, L₂, and L₃ are each free of any carbonyl group.

A case where the formula (1) has a structure represented by thefollowing general formula (3) is excluded,

provided that, X₁, X₂, A₁, A₂, L₁, and L₂ in the formula (3) has thesame meaning X₁, X₂, A₁, A₂, L₁, and L₂ in the formula (1),respectively.

In the formula (3), Y₁, Y₂, and Y₃ each represent an alkyl group having1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving a ring formed of 3 to 20 carbon atoms, an alkoxy group having 1to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, asilyl group having 3 to 20 carbon atoms, a substituted or unsubstitutedaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted aromatic heterocyclic group which hasa ring formed of 3 to 24 atoms and which is linked with a benzene ringa, b, or c through a carbon-carbon bond, the number of each of Y₁ and Y₃is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

A case where the formula (2) has a structure represented by thefollowing general formula (4) is excluded,

provided that, X₁, X₂, R₁, L₁, L₃, and n in the formula (4) has the samemeaning X₁, X₂, A₁, L₁, L₃, and n in the formula (2), respectively.

In the formula (4), Y₁, Y₂, and Y₃ each represent an alkyl group having1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving a ring formed of 3 to 20 carbon atoms, an alkoxy group having 1to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, asilyl group having 3 to 20 carbon atoms, a substituted or unsubstitutedaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted aromatic heterocyclic group which hasa ring formed of 3 to 24 atoms and which is linked with the benzene ringa, b, or c through a carbon-carbon bond, the number of each of Y₁ and Y₃is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.]

In addition, the present invention provides an organic EL device havingone or more organic thin film layers including a light emitting layerbetween a cathode and an anode in which at least one layer of theorganic thin film layers contains a material for an organic EL device asa compound having a π-conjugated heteroacene skeleton crosslinked with acarbon atom, nitrogen atom, oxygen atom, or sulfur atom. A material foran organic EL device represented by the above formula (1) or (2) ispreferably used as the material for an organic EL device of the presentinvention.

Further, the material for an organic EL device is effective also as amaterial for an organic electron device such as an organic solar cell,organic semiconductor laser, a sensor using organic matter, or anorganic TFT.

Effects of the Invention

According to the present invention, there can be provided an organic ELdevice which shows high luminous efficiency, is free of any pixeldefect, and has a long lifetime, and a material for an organic EL devicefor realizing the device.

BEST MODE FOR CARRYING OUT THE INVENTION

A material for an organic EL device of the present invention isrepresented by the following general formula (1) or

[In the formulae (1) and (2), Ar₁, Ar₂, and Ar₃ each independentlyrepresent a substituted or unsubstituted aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms or a substituted orunsubstituted aromatic heterocyclic group having a ring formed of 3 to24 atoms, provided that, Ar₁, Ar₂, and Ar₃ each may have one substituentY or multiple substituents Ys, in the case of multiple substituents Ys,the substituent Ys may be different from each other, Y represents analkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withAr₁, Ar₂, or Ar₃ through a carbon-carbon bond.

In the formulae (1) and (2), X₁, X₂, X₃, and X₄ each independentlyrepresent O, S, N—R₁, or CR₂R₃.

In the formulae (1) and (2), R₁, R₂, and R₃ each independently representan alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon, atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₁ and X₂ representN—R₁, o and p each represent 0, and q represents 1, or when both X₁ andX₃ represent N—R₁, p and q each represent 0, and o represents 1, atleast one R₁ represents a substituted or unsubstituted, monovalent fusedaromatic heterocyclic group having a ring formed of 8 to 24 atoms.

In the formulae (1) and (2), o, p, and q each represent 0 or 1, srepresents 1, 2, or 3, when s represents 2 or 3, and the generalformulae (1) and (2) are each represented as the following.

When s represents 2

When s represents 3

n represents 2, 3, or 4, and the material represented by the formula (2)includes a dimer using L₃ as a linking group for n=2, a trimer using L₃as a linking group for n=3, or a tetramer using L₃ as a linking groupfor n=4.

In the formulae (1) and (2), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with Ar₁ through a carbon-carbon bond.

In the formula (1), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with Ar₃ through a carbon-carbon bond, provided that, when bothX₁ and X₂ represent CR₂R₃, o and p each represent 0, q represents 1, andboth L₁ and L₂ represent substituted or unsubstituted, monovalent ordivalent aromatic hydrocarbon groups each having a ring formed of 6 to24 carbon atoms, or when both X₁ and X₃ represent CR₂R₃, p and q eachrepresent 0, o represents 1, and both L₁ and L₂ represent substituted orunsubstituted, monovalent or divalent aromatic hydrocarbon groups eachhaving a ring formed of 6 to 24 carbon atoms, a case where L₁ and L₂ aresimultaneously linked at para positions with respect to Ar₂ is excluded.

In the formula (2), when n represents 2, L₃ represents a single bond, analkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with Ar₃ through a carbon-carbon bond, when nrepresents 3, L₃ represents a trivalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, trivalent cycloalkane having aring formed of 3 to 20 carbon atoms, a trivalent silyl group having 1 to20 carbon atoms, a substituted or unsubstituted, trivalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, trivalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with Ar₃through a carbon-carbon bond, or when n represents 4, L₃ represents atetravalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, tetravalent cycloalkane having a ring formed of 3 to 20carbon atoms, a silicon atom, a substituted or unsubstituted,tetravalent aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted, tetravalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with Ar₃ through a carbon-carbon bond, provided that, when bothX₁ and X₂ represent CR₂R₃, o and p each represent 0, g represents 1, andboth L₁ and L₃ represent substituted or unsubstituted, monovalent,divalent, trivalent, or tetravalent aromatic hydrocarbon groups eachhaving a ring formed of 6 to 24 carbon atoms, or when both X₁ and X₃represent CR₂R₃, p and q each represent 0, o represents 1, and both L₁and L₃ represent substituted or unsubstituted, monovalent, divalent,trivalent, or tetravalent aromatic hydrocarbon groups each having a ringformed of 6 to 24 carbon atoms, a case where L₁ and L₃ aresimultaneously linked at para positions with respect to Ar₂ is excluded.

In the formulae (1) and (2), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstitutedaromatic heterocyclic group which has a ring formed of 3 to 24 atoms andwhich is linked with L₁ through a carbon-carbon bond, provided that,when L₁ represents an alkyl or alkylene group having 1 to 20 carbonatoms, a case where A₁ represents a hydrogen atom is excluded.

In the formula (1), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withL₂ through a carbon-carbon bond, provided that, when L₂ represents analkyl or alkylene group having 1 to 20 carbon atoms, a case where A₂represents a hydrogen atom is excluded, and, when X₁ and X₂ eachrepresent O, S, or CR₂R₃, o and p each represent 0, q represents 1, andboth L₁ and L₂ represent single bonds, or when both X₁ and X₃ eachrepresent O, S, or CR₂R₃, p and q each represent 0, o represents 1, andboth L₁ and L₂ represent single bonds, a case where A₁ and A₂simultaneously represent hydrogen atoms is excluded.

In the formulae (1) and (2), A₁, A₂, L₁, L₂, and L₃ are each free of anycarbonyl group.

A case where the formula (1) has a structure represented by thefollowing general formula (3) is excluded,

provided that, X₁, X₂, A₁, A₂, L₁, and L₂ in the formula (3) has thesame meaning X₁, X₂, A₁, A₂, L₁, and L₂ in the formula (1),respectively.

In the formula (3), Y₁, Y₂, and Y₃ each represent an alkyl group having1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving a ring formed of 3 to 20 carbon atoms, an alkoxy group having 1to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, asilyl group having 3 to 20 carbon atoms, a substituted or unsubstitutedaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted aromatic heterocyclic group which hasa ring formed of 3 to 24 atoms and which is linked with a benzene ringa, b, or c through a carbon-carbon bond, the number of each of Y₁ and Y₃is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

A case where the formula (2) has a structure represented by thefollowing general formula (4) is excluded,

provided that, X₁, X₂, A₁, L₁, L₃, and n in the formula (4) has the samemeaning X₁, X₂, A₁, L₁, L₃, and n in the formula (2), respectively.

In the formula (4), Y₁, Y₂, and Y₃ each represent an alkyl group having1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving a ring formed of 3 to 20 carbon atoms, an alkoxy group having 1to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, asilyl group having 3 to 20 carbon atoms, a substituted or unsubstitutedaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted aromatic heterocyclic group which hasa ring formed of 3 to 24 atoms and which is linked with a benzene ringa, b, or c through a carbon-carbon bond, the number of each of Y₁ and Y₃is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

When the benzene ring a is substituted by multiple Y₁s, the benzene ringb is substituted by multiple Y₂s, or the benzene ring c is substitutedby multiple Y₃s in the formulae (3) and (4), each of the rings isrepresented as shown below.

The material for an organic EL device represented by the general formula(1) is preferably a material for an organic EL device represented by anyone of the following general formulae (5), (7) to (9), (13), (15), and(17), and the material for an organic EL device represented by thegeneral formula (2) is preferably a material for an organic EL devicerepresented by any one of the following general formulae (6), (10) to(12), (14), (1.6), and (18).

[In the formulae (5) and (6), X₅ and X₆ each independently represent O,S, N—R₁, or CR₂R₃.

In the formulae (5) and (6), R₁, R₂, and R₃ each independently representan alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₅ and X₆ representN—R₁, at least one R₁ represents a substituted or unsubstituted,monovalent fused aromatic heterocyclic group having a ring formed of 8to 24 atoms.

In the formula (6), n represents 2, 3, or 4, and the materialrepresented by the formula (6) includes a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4.

In the formulae (5) and (6), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formula (5), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with the benzene ring c through a carbon-carbon bond, providedthat, when both X₅ and X₆ represent CR₂R₃ and both L₁ and L₂ representsubstituted or unsubstituted, monovalent or divalent aromatichydrocarbon groups each having a ring formed of 6 to 24 carbon atoms, acase where L₁ and L₂ are simultaneously linked at para positions withrespect to a benzene ring b is excluded.

In the formulae (6), when n represents 2, L₃ represents a single bond,an alkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with a benzene ring c through a carbon-carbonbond, when n represents 3, L₃ represents a trivalent alkane having 1 to20 carbon atoms, a substituted or unsubstituted, trivalent cycloalkanehaving a ring formed of 3 to 20 carbon atoms, a trivalent silyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted, trivalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, trivalent aromatic heterocyclic groupwhich has 3 to 24 atoms and which is linked with a benzene ring cthrough a carbon-carbon bond, or when n represents 4, L₃ represents atetravalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, tetravalent cycloalkane having a ring formed of 3 to 20carbon atoms, a silicon atom, a substituted or unsubstituted,tetravalent aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted, tetravalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with the benzene ring c through a carbon-carbon bond, providedthat, when both X₅ and X₆ represent CR₂R₃ and both L₁ and L₃ representsubstituted or unsubstituted, monovalent, divalent, trivalent, ortetravalent aromatic hydrocarbon groups each having a ring formed of 6to 24 carbon atoms, a case where L₁ and L₃ are simultaneously linked atpara positions with respect to the benzene ring b is excluded.

In the formulae (5) and (6), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formula (5), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when X₅ and X₆ each represent O, S, or CR₂R₃ and bothL₁ and L₂ represent single bonds, a case where A₁ and A₂ simultaneouslyrepresent hydrogen atoms is excluded.

In the formulae (5) and (6), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₃ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (5) and (6), A₁, A₂, L₁, L₂, and L₃ are each free of anycarbonyl group.]

[In the formulae (7) to (12), X₇, X₈, X₉, X₁₀, X₁₁, and X₁₂ eachindependently represent O, S, N—R₁, or CR₂R₃.

In the formulae (7) to (12), R₁, R₂, and R₃ each independently representan alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₇ and X₈, both X₉ andX₁₀, and both X₁₁ and X₁₂ represent N—R₁, at least one R₁ represents asubstituted or unsubstituted, monovalent fused aromatic heterocyclicgroup having a ring formed of 8 to 24 atoms.

In the formulae (10) to (12), n represents 2, 3, or 4, and the materialrepresented by any one of the formulae (10) to (12) includes a dimerusing L₃ as a linking group for n=2, a trimer using L₃ as a linkinggroup for n=3, or a tetramer using L₃ as a linking group for n=4.

In the formulae (7) to (12), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formulae (7) to (9), L₂ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond, providedthat, when both X₇ and X₈, both X₉ and X₁₀, or both X₁₁ and X₁₂,represent CR₂R₃ and both L₁ and L₂ represent substituted orunsubstituted, monovalent or divalent aromatic hydrocarbon groups eachhaving a ring formed of 6 to 24 carbon atoms, a case where L₁ and L₂ aresimultaneously linked at para positions with respect to a benzene ring bis excluded.

In the formulae (10) to (12), when n represents 2, L₃ represents asingle bond, an alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkylene group having a ring formed of3 to 20 carbon atoms, a divalent silyl group having 2 to 20 carbonatoms, a substituted or unsubstituted, divalent aromatic hydrocarbongroup having a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, divalent aromatic heterocyclic group which has a ringformed of 3 to 24 atoms and which is linked with the benzene ring cthrough a carbon-carbon bond, when n represents 3, L₃ represents atrivalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent cycloalkane having a ring formed of 3 to 20carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted, trivalent aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, trivalent aromatic heterocyclic group which has 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, or when n represents 4, L₃ represents a tetravalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, asilicon atom, a substituted or unsubstituted, tetravalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, tetravalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond, provided that, when both X₇and X₈, both X₉ and X₁₀, or both X₁₁ and X₁₂, represent CR₂R₃ and bothand L₃ represent substituted or unsubstituted, monovalent, divalent,trivalent, or tetravalent aromatic hydrocarbon groups each having a ringformed of 6 to 24 carbon atoms, a case where L₁ and L₃ aresimultaneously linked at para positions with respect to the benzene ringb is excluded.

In the formulae (7) to (12), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A represents ahydrogen atom is excluded.

In the formulae (7) to (9), A₂ represents a hydrogen atom, a substitutedor unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when both X₇ and X₈, both X₉ and X₁₀, or both X₁₂ andX₁₂, represent O, S, or CR₂R₃ and both L₁ and L₂ represent single bonds,a case where A₁ and A₂ simultaneously represent hydrogen atoms isexcluded.

In the formulae (7) to (12), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (7) to (12), A₁, A₂, L₁, L₂, and L₃ are each free of anycarbonyl group.]

[In the formulae (13) and (14), X₁₃ and X₁₄ each independently representO, S, N—R₁, or CR₂R₃.

In the formulae (13) and (14), R₁, R₂, and R₃ each independentlyrepresent an alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₁₃ and X₁₄ representN—R₁, at least one R₁ represents a substituted or unsubstituted,monovalent fused aromatic heterocyclic group having a ring formed of 8to 24 atoms.

In the formula (14), n represents 2, 3, or 4, and the materialrepresented by the formula (14) includes a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4.

In the formulae (13) and (14), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formula (13), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond, providedthat, when both X₁₃ and X₁₄ represent CR₂R₃ and both L₁ and L₂ representsubstituted or unsubstituted, monovalent or divalent aromatichydrocarbon groups each having a ring formed of 6 to 24 carbon atoms, acase where L₁ and L₂ are simultaneously linked at para positions withrespect to a benzene ring b is excluded.

In the formula (14), when n represents 2, L₃ represents a single bond,an alkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond, provided that, when both X₁₃ and X₁₄ represent CR₂R₃and both L₁ and L₃ represent substituted or unsubstituted, monovalent,divalent, trivalent, or tetravalent aromatic hydrocarbon groups eachhaving a ring formed of 6 to 24 carbon atoms, a case where L₁ and L₃ aresimultaneously linked at para positions with respect to the benzene ringb is excluded.

In the formulae (13) and (14), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formula (13), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when X₁₃ and X₁₄ each represent O, S, or CR₂R₃, andboth L₁ and L₂ represent single bonds, a case where A₃ and A₂simultaneously represent hydrogen atoms is excluded.

In the formulae (13) and (14), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (13) and (14), A₁, A₂, L₁, L₂, and L₃ are each free ofany carbonyl group.]

The compounds represented by the general formulae (5) and (6) are eachpreferably a benzofurano dibenzofuran derivative represented by one ofthe following general formulae (15) and (16).

[In the formula (16), n represents 2, 3, or 4, and the materialrepresented by the formula (16) includes a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4.

In the formulae (15) and (16), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formula (15), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond.

In the formula (16), when n represents 2, L₃ represents a single bond,an alkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond.

In the formulae (15) and (16), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formula (15), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when both L₁ and L₂ represent single bonds, a casewhere A₁ and A₂ simultaneously represent hydrogen atoms is excluded.

In the formulae (15) and (16), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (15) and (16), A₁, A₂, L₁, L₂, and L₃ are each free ofany carbonyl group.]

The compounds represented by the general formulae (9) and (12) are eachpreferably a benzofurano dibenzofuran derivative represented by one ofthe following general formulae (17) and (18).

[In the formula (18), n represents 2, 3, or 4, and the materialrepresented by the formula (18) includes a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4.

In the formulae (17) and (18), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formula (17), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond.

In the formula (18), when n represents 2, L₃ represents a single bond,an alkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond.

In the formulae (17) and (18), A₂ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formula (17), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when both L₁ and L₂ represent single bonds, a casewhere A₁ and A₂ simultaneously represent hydrogen atoms is excluded.

In the formulae (17) and (18), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (17) and (18), A₁, A₂, L₁, L₂, and L₃ are each free ofany carbonyl group.]

In the general formulae (1) to (18), specific examples of each group aredescribed below.

Examples of the substituted or unsubstituted aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms represented by Ar₁ to Ar₃,Y, Y₁ to Y₃, R₁ to R₃, L₁ to L₃, and A₁ and A₂ include residues havingcorresponding valencies such as substituted or unsubstituted benzene,naphthalene, biphenyl, terphenyl, fluorene, phenanthrene, triphenylene,perylene, chrysene, fluoranthene, benzofluorene, bnezotriphenylene,benzochrysene, and anthracene. Preferred are benzene, naphthalene,biphenyl, terphenyl, fluorene, and phenanthrene.

Examples of the substituted or unsubstituted aromatic heterocyclic grouphaving a ring formed of 3 to 24 atoms represented by Ar₁ to Ar₃, Y, Y₁to Y₃, R₁ to R₃, L₁ to L₃, and A₁ and A₂ include residues havingcorresponding valencies such as pyridine, pyridazine, pyrimidine,pyrazine, 1,3,5-triazine, carbazole, dibenzofuran, dibenzothiophene,phenoxazine, phenothiazine, and dihydroacridine. Preferred are pyridine,pyridazine, pyrimidine, pyrazine, carbazole, dibenzofuran,dibenzothiophene, phenoxazine, and dihydroacridine. In addition,examples of at least one substituted or unsubstituted, monovalent fusedaromatic heterocyclic group having a ring formed of 8 to 24 atomsrepresented by R₁ include aromatic heterocyclic groups each having afused structure in examples of the aromatic heterocyclic groups.

Examples of the alkyl group, alkylene group, and trivalent ortetravalent alkane, each of which has 1 to 20 carbon atoms representedby Y, Y₁ to Y₃, L₁ to L₃, and R₁ to R₃ include a methyl group, an ethylgroup, a propyl group, an isopropyl group, an n-butyl group, an s-butylgroup, a t-butyl group, an isobutyl group, an n-pentyl group, an n-hexylgroup, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decylgroup, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, ann-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, ann-heptadecyl group, an n-octadecyl group, an neopentyl group, a1-methylpentyl group, a 2-methylpentyl group, a 1-pentylhexyl group, a1-butylpentyl group, a 1-heptyloctyl group, and a 3-methylpentyl groupor groups obtained by allowing those groups to have two to fourvalencies. Preferred are a methyl group, an ethyl group, a propyl group,an isopropyl group, an n-butyl group, an s-butyl group, an isobutylgroup, a t-butyl group, n-pentyl group, an n-hexyl group, an n-heptylgroup, an n-octyl group, an n-nonyl group, an n-decyl group, ann-undecyl group, an n-dodecyl group, an n-tridecyl group, ann-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, ann-heptadecyl group, an n-octadecyl group, an neopentyl group, a1-methylpentyl group, a 1-pentylhexyl group, a 1-butylpentyl group, anda 1-heptyloctyl group.

Examples of the substituted or unsubstituted cycloalkyl group,cycloalkylene group, and trivalent or tetravalent cycloalkane, each ofwhich has a ring formed of 3 to 20 carbon atoms, represented by Y, Y₁ toY₃, L₁ to L₃, R₁ to R₃, and A₁ and A₂ include a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, and groupsobtained by allowing those group to have two to four valencies.Preferred are a cyclobutyl group, a cyclopentyl group, and a cyclohexylgroup.

Examples of the alkoxy group having 1 to 20 carbon atoms and representedby Y, Y₁ to Y₃ include a methoxy group, an ethoxy group, a methoxygroup, an i-propoxy group, an n-propoxy group, an n-butoxy group, ans-butoxy group, and a t-butoxy group. Preferred are a methoxy group, anethoxy group, a methoxy group, an i-propoxy group, and an n-propoxygroup.

Examples of the silyl group having 1 to 20 carbon atoms represented byY, Y₁ to Y₃, L₁ to L₃, R₁ to R₃, and A₁ and A₂ include a trimethyl silylgroup, a triethyl silyl group, a tributyl silyl group, a trioctyl silylgroup, a triisobutyl silyl group, a dimethylethyl silyl group, adimethylisopropyl silyl group, a dimethylpropyl silyl group, adimethylbutyl silyl group, a dimethyltertiary butyl silyl group, adiethylisopropyl silyl group, a phenyldimethyl silyl group, adiphenylmethyl silyl group, a diphenyl tertiary butyl group, a triphenylsilyl group, and groups obtained by allowing those groups to have two orthree valencies. Preferred are a trimethyl silyl group, a triethyl silylgroup, and a tributyl silyl group.

Examples of the aralkyl group having 7 to 24 carbon atoms represented byY, Y₁ to Y₃, and R₁ to R₃ include a benzyl group, a phenethyl group, anda phenylpropyl group.

Examples of the substituent that can be substituted for the each groupin the general formulae (1) to (18) include alkyl groups each having 1to 10 carbon atoms (such as a methyl group, an ethyl group, a propylgroup, an isopropyl group, an n-butyl group, an s-butyl group, anisobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, ann-heptyl group, an n-octyl group, a hydroxymethyl group, a1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxyisobutyl group,a 1,2-dihydroxyethyl group, a 1,3-dihydroxyisopropyl group, a2,3-dihydroxy-t-butyl group, a 1,2,3-trihydroxypropyl group, achloromethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a2-chloroisobutyl group, a 1,2-dichloroethyl group, a1,3-dichloroisopropyl group, a 2,3-dichloro-t-butyl group, a1,2,3-trichloropropyl group, a bromomethyl group, a 1-bromoethyl group,a 2-bromoethyl group, a 2-bromoisobutyl group, a 1,2-dibromoethyl group,a 1,3-dibromoisopropyl group, a 2,3-dibromo-t-butyl group, a1,2,3-tribromopropyl group, a iodomethyl group, a 1-iodoethyl group, a2-iodoethyl group, a 2-iodoisobutyl group, a 1,2-diiodoethyl group, a1,3-diiodoisopropyl group, a 2,3-diiodo-t-butyl group, a1,2,3-triiodopropyl group, an aminomethyl group, a 1-aminoethyl group, a2-aminoethyl group, a 2-aminoisobutyl group, a 1,2-diaminoethyl group, a1,3-diaminoisopropyl group, a 2,3-diamino-t-butyl group, a1,2,3-triaminopropyl group, a cyanomethyl group, a 1-cyanoethyl group, a2-cyanoethyl group, a 2-cyanoisobutyl group, a 1,2-dicyanoethyl group,1,3-dicyanoisopropyl group, a 2,3-dicyano-t-butyl group, a1,2,3-tricyanopropyl group, a nitromethyl group, a 1-nitroethyl group, a2-nitroethyl group, a 2-nitroisobutyl group, a 1,2-dinitroethyl group, a1,3-dinitroisopropyl group, a 2,3-dinitro-t-butyl group, and a1,2,3-trinitropropyl group), cycloalkyl groups each having a ring formedof 3 to 40 carbon atoms (such as a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexylgroup, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group,and a 2-norbornyl group), alkoxy groups each having 1 to 6 carbon atoms(such as an ethoxy group, a methoxy group, an i-propoxy group, ann-propoxy group, an s-butoxy group, a t-butoxy group, a pentoxy group,and a hexyloxy group), cycloalkoxy groups each having a ring formed of 3to 10 carbon atoms (such as a cyclopentoxy group and a cyclohexyloxygroup), aromatic hydrocarbon groups each having a ring formed of 6 to 40carbon atoms, aromatic heterocyclic groups having a ring formed of 3 to40 atoms, amino groups substituted with aromatic hydrocarbon groupshaving a ring formed of 6 to 40 carbon atoms, ester groups havingaromatic hydrocarbon groups having a ring formed of 6 to 40 carbonatoms, an ester group, cyano group, nitro group, and halogen atom, eachof which has an alkyl group having 1 to 6 carbon atoms.

Of those, alkyl groups each having 1 to 6 carbon atoms, a phenyl group,a pyridyl group, a carbazolyl group, and a dibenzofuranyl group arepreferred and the number of substituents is preferably 1 or 2.

In the material for an organic EL device represented by the generalformula (2), (6), (10) to (12), (14), (16), or (18), n preferablyrepresents 2.

In the general formula (5), (7) to (9), (13), (15), or (17), the totalnumber of the substituents represented by Y₁, Y₂, and Y₂ is preferably 3or less, and the total number of the substituents represented by Y₁, Y₂,and Y₃ in the structure of [ ]_(n) in the general formula (6), (10) to(12), (14), (16) or (18) is preferably 3 or less.

In the general formula (1) or (2), X₁ and X₂, or X₃ and X₄ are eachrepresented by N—R_(a). N—R₁ of X₁ and N—R₁ of X₂, or N—R₁ of X₃ andN—R₁ of X₄ may be preferably different from each other.

In the general formula (5) or (6), X₅ and X₆ are each represented byN—R₁. N—R₁ of X₅ and N—R₁ or X₆ may be preferably different from eachother.

In the general formulae (7) to (12), X₇ and X₈, X₉ and X₁₀, or X₁₁ andX₁₂, are each represented by N—R₁. N—R₁ of X₇ and N—R₁ of X₈, N—R₁ of X₉and N—R₁ of X₁₀, or N—R₁ of X₁₃ and N—R₁ of X₁₂, may be preferablydifferent from each other.

In the general formula (13) or (14), X₁₃ and X₁₄ are each represented byN—R₃. N—R₁ of X₁₃ and N—R₁ or X₁₄ may be preferably different from eachother.

In the general formulae (1), (2), (5) to (14), both X₁ and X₂, both X₃and X₄, both X₅ and X₆, both X₇ and X₈, both X₉ and X₁₀, both X₁₁ andX₁₂, both X₁₃ and X₁₄, and both X₁₅ and X₁₆ preferably represent oxygenatoms.

Specific examples of the material for an organic EL device representedby any one of the general formulae (1), (2), (5) to (18) of the presentinvention are shown below. However, the present invention is not limitedto these exemplified compounds.

Next, an organic EL device of the present invention will be described.

The organic EL device of the present invention has one or more organicthin film layers including a light emitting layer between a cathode andan anode, and at least one layer of the organic thin film layerscontains a material for an organic EL device serving as a compoundhaving a π-conjugated heteroacene skeleton crosslinked with a carbonatom, nitrogen atom, oxygen atom, or sulfur atom. Specific examples ofthe π-conjugated heteroacene skeleton are shown below.

In addition to the foregoing, a π-conjugated heteroacene skeletoncrosslinked with a combination of two or more of a carbon atom, anitrogen atom, an oxygen atom, and a sulfur atom is also permitted.Specific examples of the π-conjugated heteroacene skeleton are shownbelow.

In addition, the above-mentioned material for an organic EL device ofthe present invention is preferably used as the material for an organicEL device.

The organic EL device may have an electron transporting layer betweenthe light emitting layer and the cathode, and the electron transportinglayer may contain the material for an organic EL device. Further, boththe light emitting layer and the electron transporting layer eachpreferably contain the material for an organic EL device.

Alternatively, the organic EL device may have a hole transporting layerbetween the light emitting layer and the anode, and the holetransporting layer may contain the material for an organic EL device.

Further, the material for an organic EL device of the present inventionis preferably incorporated into at least the light emitting layer. Whenthe material is used in the light emitting layer, the lifetime of theorganic EL device can be lengthened. When the material is used in theelectron transporting layer or the electron injecting layer, the voltageat which the device is driven can be reduced. The material is preferablyincorporated into each of two or more layers including the lightemitting layer and the electron transporting layer or the electroninjecting layer at the same time because both the reduced voltage andthe lengthened lifetime can be achieved.

In particular, in addition to the electron transporting layer or theelectron injecting layer, the light emitting layer preferably includethe material for an organic EL device of the present invention as a hostmaterial. The light emitting layer preferably includes the material foran organic EL device represented by the general formula (5) or (6), orthe general formula (9) or (12) as a host material, and more preferablyincludes the material for an organic EL device represented by thegeneral formula (15) or (16), or the general formula (17) or (18) as ahost material.

A multi-layer type organic EL device is obtained by laminating multiplelayers; for example, the device is formed of an anode, a holetransporting layer (a hole injecting layer), a light emitting layer, anda cathode, of an anode, a light emitting layer, an electron transportinglayer (an electron injecting layer), and a cathode, of an anode, a holetransporting layer (a hole injecting layer), a light emitting layer, anelectron transporting layer (an electron injecting layer), and acathode, or of an anode, a hole transporting layer (a hole injectinglayer), a light emitting layer, a hole barrier layer, an electrontransporting layer (an electron injecting layer), and a cathode.

In the organic EL device of the present invention, the light emittinglayer preferably contains the material for an organic EL device as ahost material. In addition, it is preferred that the light emittinglayer be composed of a host material and a phosphorescent material, andthe host material be the material for an organic EL device.

In addition, the material for an organic EL device may be a hostmaterial to be used together with a phosphorescent material, or may bean electron transporting material to be used together with aphosphorescent material. The material has a triplet energy gap ofpreferably 2.2 to 3.2 eV, or more preferably 2.5 to 3.2 eV.

The phosphorescent material is preferably a compound containing iridium(Ir), osmium (Os), ruthenium (Ru), or platinum (Pt) because the compoundhas a high phosphorescent quantum yield, and can additionally improvethe external quantum efficiency of the light emitting device. Thematerial is more preferably a metal complex such as an iridium complex,an osmium complex, a ruthenium complex, or a platinum complex. Of those,the iridium complex and the platinum complex are still more preferable,and an orthometalated iridium complex is most preferable. Specificexamples of the metal complex such as an iridium complex, an osmiumcomplex, a ruthenium complex, or a platinum complex are shown below.

In addition, the organic EL device of the present invention ispreferably such that the light emitting layer contains a host materialand a phosphorescent material, and contains a metal complex having alocal maximum luminous wavelength of 500 nm or less. Further, thematerial of the present invention can be used together with afluorescent dopant. The material can be used together with a blue,green, or red fluorescent dopant. In particular, the material can bemore preferably used together with the blue or green fluorescent dopant.Further, the material can be preferably used also as an electrontransporting material for a fluorescent organic EL device.

The organic EL device of the present invention preferably has areductive dopant in an interfacial region between the cathode and anorganic thin layer (for example, an electron injecting layer or a lightemitting layer). Examples of the reductive dopant include at least onekind selected from an alkali metal, an alkali metal complex, an alkalimetal compound, an alkaline earth metal, an alkaline earth metalcomplex, an alkaline earth metal compound, a rare earth metal, a rareearth metal complex, and a rare earth metal compound.

Preferred examples of the alkali metal include an alkali metal having awork function of 2.9 eV or less, such as Na having a work function of2.36 eV, K having a work function of 2.28 eV, Rb having a work functionof 2.16 eV, and Cs having a work function of 1.95 eV. Of those, K, Rb,and Cs are more preferable, Rb or Cs is still more preferable, and Cs ismost preferable.

Preferred examples of the alkali earth metal include an alkali earthmetal having a work function of 2.9 eV or less, such as Ca having a workfunction of 2.9 eV, Sr having a work function of 2.0 to 2.5 eV, and Bahaving a work function of 2.52 eV.

Preferred examples of the rare earth metal include a rare earth metalhaving a work function of 2.9 eV or less, such as Sc, Y, Ce, Tb, and Yb.

Of those metals, a preferable metal has a particularly high reductiveability, so improvement of light emission intensity and long life oforganic EL device can be attained by adding a relatively small amount ofthe metal to an electron injecting region.

Examples of the alkali metal compound include an alkali oxide such asLi₂O, Cs₂O, or K₂O, and an alkali halide such as LiF, NaF, CsF, or KF.Of those, LiF, Li₂O, or NaF is preferable.

Examples of the alkali earth metal compound include BaO, SrO, CaO, andmixtures thereof such as Ba_(m)Sr_(1-m)O (0<m<1) and Ba_(m)Ca_(1-m)O(0<m<1). Of those, BaO, SrO, and CaO are preferable.

Examples of the rare earth metal compound include YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. Of those, YbF₃, ScF₃, and TbF₃ arepreferable.

The alkali metal complex, alkali earth metal complex, and rare earthmetal complex are not particularly limited as long as they each includeas a metal ion at least one of alkali metal ions, alkali earth metalions, and rare earth metal ions. Meanwhile, preferable examples of aligand include, but not limited to, quinolinol, benzoquinolinol,acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole,hydroxydiaryloxadiazole, hydroxydiarylthiadiazole,hydroxyphenylpyridine, hydroxyphenylbenzoimidazole,hydroxybenzotriazole, hydroxyfluborane, bipyridyl, phenanthroline,phthalocyanine, porphyrin, cyclopentadiene, β-diketones, azomethines,and derivatives thereof.

For the addition form of the reductive dopant, it is preferable that thereductive dopant be formed in a shape of a layer or an island in theinterfacial region. A preferable example of the forming method includesa method in which an organic substance which is a light emittingmaterial or an electron injecting material for forming the interfacialregion is deposited at the same time as the reductive dopant isdeposited by a resistant heating deposition method, thereby dispersingthe reductive dopant in the organic substance. The disperseconcentration by molar ratio of the organic compound to the reductivedopant is 100:1 to 1:100, and is preferably 5:1 to 1:5.

In a case where the reductive dopant is formed into the shape of alayer, the light emitting material or electron injecting material whichserves as an organic layer in the interface is formed into the shape ofa layer. After that, the reductive dopant is solely deposited by theresistant heating deposition method to form a layer preferably having athickness of 0.1 to 15 nm.

In a case where the reductive dopant is formed into the shape of anisland, the light emitting material or electron injecting material whichserves as an organic layer in the interface is formed into the shape ofan island. After that, the reductive dopant is solely deposited by theresistant heating deposition method to form an island preferably havinga thickness of 0.05 to 1 nm.

When the organic EL device of the present invention has an electroninjecting layer between the light emitting layer and the cathode, anelectron transporting material to be used in the electron injectinglayer is preferably an aromatic heterocyclic compound containing one ormore heteroatoms in anyone of its molecules, or particularly preferablya nitrogen-containing ring derivative.

The nitrogen-containing ring derivative is preferably, for example, anitrogen-containing ring metal chelate complex represented by thefollowing general formula (A).

R² to R⁷ each independently represent a hydrogen atom, a halogen atom,an amino group, a hydrocarbon group each having 1 to 40 carbon atoms, analkoxy group, an aryloxy group, an alkoxycarbonyl group, or aheterocyclic group, each of which may be substituted.

Examples of the halogen atom represented by R² to R⁷ include a fluorineatom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the amino group that may be substituted and represented byR² to R⁷ include an alkylamino group, an arylamino group, and anaralkylamino group. Examples of the alkyl group in the alkylamino groupinclude alkyl groups each having 1 to 40 carbon atoms such as a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonylgroup, an n-decyl group, an n-undecyl group, an n-dodecyl group, ann-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, ann-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, anneopentyl group, a 1-methylpentyl group, a 2-methylpentyl group, a1-pentylhexyl group, a 1-butylpentyl group, a 1-heptyloctyl group, a3-methylpentyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, a iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 1,2-dinitroethylgroup, a 2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.Preferred are alkyl groups each having 1 to 20 carbon atoms and morepreferred are alkyl groups each having 1 to 10 carbon atoms.

Examples of the aryl group in the arylamino group include aryl groupseach having a ring formed of 6 to 40 carbon atoms such as a phenylgroup, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, 4-phenanthryl group, a9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, a an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group. Preferred are aryl groups each havinga ring formed of 6 to 20 carbon atoms and more preferred are aryl groupseach having a ring formed of 6 to 10 carbon atoms.

Examples of the aralkyl group in the aralkylamino group include aralkylgroups each having 7 to 40 carbon atoms such as a benzyl group, a1-phenylethyl group, a 2-phenylethyl group, a 1-phenyl isopropyl group,a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethylgroup, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, aβ-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, a1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethyl group, a p-methylbenzylgroup, an m-methylbenzyl group, an o-methylbenzyl group, ap-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzyl group,a p-bromobenzyl group, an m-bromobenzyl group, an o-bromobenzyl group, ap-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, ap-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzylgroup, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzylgroup, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzylgroup, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzylgroup, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group. Preferred are aralkyl groups eachhaving 7 to 20 carbon atoms and more preferred are aralkyl groups eachhaving 7 to 10 carbon atoms.

Examples of the hydrocarbon groups each having 1 to 40 carbon atomsrepresented by R² to R⁷ include substituted or unsubstituted alkylgroups, alkenyl groups, cycloalkyl groups, aryl groups, and aralkylgroups.

As the alkyl groups, the same examples of the alkyl groups in theabove-mentioned alkylamino group are given, and alkyl groups each having1 to 20 carbon atoms are preferred and alkyl groups each having 1 to 10carbon atoms are more preferred.

Examples of the alkenyl group include alkenyl groups each having 2 to 40carbon atoms such as a vinyl group, an allyl group, a 1-butenyl group, a2-butenyl group, a 3-butenyl group, a 1,3-butanedienyl group, a1-methylvinyl group, a styryl group, a 2,2-diphenyl vinyl group, a1,2-diphenyl vinyl group, a 1-methylaryl group, a 1,1-dimethylarylgroup, a 2-methylallyl group, a 1-phenylallyl group, a 2-phenylallylgroup, a 3-phenylallyl group, a 3,3-diphenylallyl group, a1,2-dimethylallyl group, a 1-phenyl-1-butenyl group, and a3-phenyl-1-butenyl group. Preferred are alkenyl groups each having 2 to20 carbon atoms and more preferred are alkenyl groups each having 2 to10 carbon atoms.

Examples of the cycloalkyl groups include cycloalkyl groups each havinga ring formed of 3 to 40 carbon atoms such as a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, a4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a1-norbornyl group, and a 2-norbornyl group. Preferred are cycloalkylgroups each having a ring formed of 3 to 10 carbon atoms are preferred.

As the aryl groups, the same examples of the aryl groups in theabove-mentioned arylamino groups are given. Preferred are aryl groupseach having a ring formed of 6 to 20 carbon atoms and more preferred arearyl groups each having a ring formed of 6 to 10 carbon atoms.

As the aralkyl groups, the same examples of the aralkyl groups in theabove-mentioned aralkylamino groups are given. Preferred are aralkylgroups each having 7 to 20 carbon atoms and more preferred are aralkylgroups each having 7 to 10 carbon atoms.

As the alkoxy group that represented by R² to R⁷ and may be substituted,the same examples of the alkyl groups in the above-mentioned alkylaminogroups are given as alkyl group moieties. Preferred are alkoxy groupseach having 1 to 20 carbon atoms and more preferred alkoxy groups eachhaving 1 to 10 carbon atoms.

As the aryloxy group that represented by R² to R⁷ and may besubstituted, aryloxy groups each having the same aryl group in theabove-mentioned arylamino group as an aryl group moiety are given.Preferred are aryl groups each having a ring formed of 6 to 20 carbonatoms and more preferred are aryl groups each having a ring formed of 6to 10 carbon atoms.

As the alkoxycarbonyl group that represented by R² to R⁷ and may besubstituted, alkoxycarbonyl groups each having the same alkyl group inthe above-mentioned alkylamino group as the alkyl group moiety aregiven. Preferred are alkoxycarbonyl groups each having 2 to 20 carbonatoms and more preferred are alkoxycarbonyl groups each having 2 to 10carbon atoms.

The heterocyclic group that represented by R² to R⁷ and may besubstituted is a monocycle or a fused ring. The heterocyclic grouppreferably has a ring formed of 1 to 20 carbon atoms, more preferablyhas a ring formed of 1 to 12 carbon atoms, and still more preferably hasa ring formed of 2 to 10 carbon atoms. The heterocyclic group is anaromatic heterocyclic group having at least one hetero atom selectedform a nitrogen atom, an oxygen atom, a sulfur atom, and selenium atom.Examples of the heterocyclic group include groups derived frompyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene,furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine,pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline,thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline,isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline,cinnoline, pteridine, acridine, phenanthroline, phanazine, tetrazole,benzoimidazole, benzoxazole, benzothiazole, benzotriazole,tetrazaindene, carbazole, and azepine. Preferred are groups derived fromfuran, thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine,quinoline, phthalazine, naphthyridine, quinoxaline, and quinazoline,more preferred are groups derived from furan, thiophene, pyridine, andquinoline, and still more preferred is a quinolinyl group.

M represents aluminum (Al), gallium (Ga), or indium (In). Indium ispreferred.

L⁴ in the formula (A) is a group represented by the following formula(A′) or (A″).

(In the formula, R⁸ to R¹² each independently represent a hydrogen atom,or a substituted or unsubstituted hydrocarbon group having 1 to 40carbon atoms, and adjacent groups may form a cyclic structure. Inaddition, R¹³ to R²⁷ each independently represent a hydrogen atom, or asubstituted or unsubstituted hydrocarbon group having 1 to 40 carbonatoms, and adjacent groups may form a cyclic structure.)

As the hydrocarbon group having 1 to 40 carbon atoms represented by R⁸to R¹² in the formula (A′) and R¹³ to R²⁷ in the formula (A″), the samespecific examples of R² to R⁷ are given.

In addition, examples of the divalent group in R⁸ to R¹² and R¹³ to R²⁷in the case where adjacent groups form a cyclic structure include atetramethylene group, a pentamethylene group, a hexamethylene group, adiphenylmethane-2,2′-diyl group, a diphenyethane-3,3′-diyl group, anddiphenylpropane-4,4′-diyl group.

Specific examples of the nitrogen-containing ring metal chelate complexrepresented by the formula (A) are shown below. However, the presentinvention is not limited to these exemplified compounds.

A nitrogen-containing heterocyclic derivative is a nitrogen-containingheterocyclic derivative composed of an organic compound having any oneof the following general formulae, and a nitrogen-containing compoundwhich is not a metal complex is also an example of the derivative.Examples of the derivative include a five- or six-membered ringcontaining a skeleton represented by the following formula (a) and aderivative of a structure represented by the following formula (b).

(In the formula (b), X represents a carbon atom or a nitrogen atom, andZ¹ and Z² each independently represent an atomic group capable offorming a nitrogen-containing heterocycle.)

An organic compound having a nitrogen-containing aromatic polycyclecomposed of a five- or six-membered ring is preferable. In the case ofsuch nitrogen-containing aromatic polycycle having multiple nitrogenatoms, a nitrogen-containing aromatic polycyclic aromatic organiccompound having a skeleton obtained by combining the above formulae (a)and (b) or the above formulae (a) and (c) is more preferable.

The nitrogen-containing group of the nitrogen-containing organiccompound is selected from, for example, nitrogen-containing heterocyclicgroups represented by the following general formulae.

(In each of the formulae, R²⁸ represents an aryl group having 6 to 40carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkylgroup having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20carbon atoms, n represents an integer of 0 to 5, and, when n representsan integer of 2 or more, multiple R²⁸s may be identical to or differentfrom each other).

Further, a preferable specific compound is, for example, anitrogen-containing heterocyclic derivative represented by the followingformula.

HAr^(a)-L⁶-Ar^(b)—Ar^(c)

(In the formula, HAr^(a) represents a nitrogen-containing heterocyclewhich has 3 to 40 carbon atoms and which may have a substituent, L⁶represents a single bond, an arylene group which has 6 to 40 carbonatoms and which may have a substituent, or a heteroarylene group whichhas 3 to 40 carbon atoms and which may have a substituent, Ar^(b)represents a divalent aromatic hydrocarbon group which has 6 to 40carbon atoms and which may have a substituent, and Ar^(c) represents anaryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent.)

HAr^(a) is selected from, for example, the following group.

L⁶ is selected from, for example, the following group.

Ar^(c) is selected from, for example, the following group.

Ar^(b) is selected from, for example, the following arylanthranil group.

(In the formulae, R²⁹ to R⁴² each independently represent a hydrogenatom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, analkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to40 carbon atoms, an aryl group which has 6 to 40 carbon atoms and whichmay have a substituent, or a heteroaryl group having 3 to 40 carbonatoms, and Ar^(d) represents an aryl group which has 6 to 40 carbonatoms and which may have a substituent, or a heteroaryl group having 3to 40 carbon atoms.)

In addition, a nitrogen-containing heterocyclic derivative in which R²⁹to R³⁶ in Ar^(b) represented by the above formula each represent ahydrogen atom is preferable.

In addition to the foregoing, the following compound (see JP 09-3448 A)is also suitably used.

(In the formula, R⁴³ to R⁴⁶ each independently represent a hydrogenatom, a substituted or unsubstituted aliphatic group, a substituted orunsubstituted alicyclic group, a substituted or unsubstitutedcarbocyclic aromatic ring group, or a substituted or unsubstitutedheterocyclic group, and X¹ and X² each independently represent an oxygenatom, a sulfur atom, or a dicyanomethylene group.)

In addition to the foregoing, the following compound (see JP 2000-173774A) is also suitably used.

In the formula, R⁴⁷, R⁴⁸, R⁴⁹, and R⁵⁰ represent groups identical to ordifferent from one another, and each represent an aryl group representedby the following formula.

(In the formula, R⁵¹, R⁵², R⁵³, R⁵⁴, and R⁵⁵ represent groups identicalto or different from one another, and each may represent a hydrogenatom, or at least one of them may represent a saturated or unsaturatedalkoxyl, alkyl, amino, or alkylamino group.)

Further, a polymer compound containing the nitrogen-containingheterocyclic group or nitrogen-containing heterocyclic derivative isalso permitted.

In addition, the electron transporting layer preferably contains atleast one of the nitrogen-containing heterocyclic derivativesrepresented by the following general formulae (201) to (203).

In the formulae (201) to (203), R⁵⁶ represents a hydrogen atom, an arylgroup which has 6 to 60 carbon atoms and which may have a substituent, apyridyl group which may have a substituent, a quinolyl group which mayhave a substituent, an alkyl group which has 1 to 20 carbon atoms andwhich may have a substituent, or an alkoxy group which has 1 to 20carbon atoms and which may have a substituent, n represents an integerof 0 to 4, R⁵⁷ represents an aryl group which has 6 to 60 carbon atomsand which may have a substituent, a pyridyl group which may have asubstituent, a quinolyl group which may have a substituent, an alkylgroup which has 1 to 20 carbon atoms and which may have a substituent,or an alkoxy group having 1 to 20 carbon atoms, R⁵⁸ and R⁵⁹ eachindependently represent a hydrogen atom, an aryl group which has 6 to 60carbon atoms and which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group which has 1 to 20 carbon atoms and which may have asubstituent, or an alkoxy group which has 1 to 20 carbon atoms and whichmay have a substituent, L⁷ represents a single bond, an arylene groupwhich has 6 to 60 carbon atoms and which may have a substituent, apyridinylene group which may have a substituent, a quinolihylene groupwhich may have a substituent, or a fluorenylene group which may have asubstituent, Ar^(e) represents an arylene group which has 6 to 60 carbonatoms and which may have a substituent, a pyridinylene group which mayhave a substituent, or a quinolinylene group which may have asubstituent, and Ar^(f) represents a hydrogen atom, an aryl group whichhas 6 to 60 carbon atoms and which may have a substituent, a pyridylgroup which may have a substituent, a quinolyl group which may have asubstituent, an alkyl group which has 1 to 20 carbon atoms and which mayhave a substituent, or an alkoxy group which has 1 to 20 carbon atomsand which may have a substituent.

In the formulae, Ar^(g) represents an aryl group which has 6 to 60carbon atoms and which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group which has 1 to 20 carbon atoms and which may have asubstituent, an alkoxy group which has 1 to 20 carbon atoms and whichmay have a substituent, or a group represented by —Ar^(e)—Ar^(f) (Ar^(e)and Ar^(f) each have the same meaning as that described above).

It should be noted that, in the formulae (201) to (203), R⁵⁶ representsa hydrogen atom, an aryl group which has 6 to 60 carbon atoms and whichmay have a substituent, a pyridyl group which may have a substituent, aquinolyl group which may have a substituent, an alkyl group which has 1to 20 carbon atoms and which may have a substituent, or an alkoxy groupwhich has 1 to 20 carbon atoms and which may have a substituent.

The aryl group which has 6 to 60 carbon atoms is preferably an arylgroup having 6 to 40 carbon atoms, or more preferably an aryl grouphaving 6 to 20 carbon atoms, and specific examples of such groupsinclude a phenyl group, a naphthyl group, an anthryl group, aphenanthryl group, a naphthacenyl group, a chrysenyl group, a pyrenylgroup, a biphenyl group, a terphenyl group, a tolyl group, at-butylphenyl group, a (2-phenylpropyl)phenyl group, a fluoranthenylgroup, a fluorenyl group, a monovalent group composed ofspirobifluorene, a perfluorophenyl group, a perfluoronaphthyl group, aperfluoroanthryl group, a perfluorobiphenyl group, a monovalent groupcomposed of 9-phenylanthracene, a monovalent group composed of9-(1′-naphthyl) anthracene, a monovalent group composed of9-(2′-naphthyl)anthracene, a monovalent group composed of6-phenylchrysene, and a monovalent group composed of9-[4-(diphenylamino)phenyl]anthracene; a phenyl group, a naphthyl group,a biphenyl group, a terphenyl group, a 9-(10-phenyl)anthryl group, a9-[10-(1′-naphthyl)]anthryl group, a 9-[10-(2′-naphthyl)]anthryl group,or the like is preferable.

The alkyl group which has 1 to 20 carbon atoms is preferably an alkylgroup having 1 to 6 carbon atoms, and specific examples of such groupinclude a methyl group, an ethyl group, a propyl group, a butyl group, apentyl group, a hexyl group, and a haloalkyl group such as atrifluoromethyl group. An alkyl group having 3 or more carbon atoms maybe linear, cyclic, or branched.

The alkoxy group which has 1 to 20 carbon atoms is preferably an alkoxygroup having 1 to 6 carbon atoms, and specific examples of such groupinclude a methoxy group, an ethoxy group, a propoxy group, a butoxygroup, a pentyloxy group, and a hexyloxy group. An alkoxy group having 3or more carbon atoms may be linear, cyclic, or branched.

Examples of the substituent of each group represented by R⁵⁶ include ahalogen atom, an alkyl group which has 1 to 20 carbon atoms and whichmay have a substituent, an alkoxy group which has 1 to 20 carbon atomsand which may have a substituent, an aryloxy group which has 6 to 40carbon atoms and which may have a substituent, an aryl group which has 6to 40 carbon atoms and which may have a substituent, or a heteroarylgroup which has 3 to 40 carbon atoms and which may have a substituent.

Examples of the halogen atom include fluorine, chlorine, bromine, andiodine.

Examples of the alkyl group which has 1 to 20 carbon atoms, the alkoxygroup which has 1 to 20 carbon atoms, and the aryl group which has 6 to40 carbon atoms include the same examples as those described above.

Examples of the aryloxy group which has 6 to 40 carbon atoms include aphenoxy group and a biphenyloxy group.

Examples of the heteroaryl group which has 3 to 40 carbon atoms includea pyrrolyl group, a furyl group, a thienyl group, a silolyl group, apyridyl group, a quinolyl group, an isoquinolyl group, a benzofurylgroup, an imidazolyl group, a pyrimidyl group, a carbazolyl group, aselenophenyl group, an oxadiazolyl group, and a triazolyl group.

n represents an integer of 0 to 4, or preferably 0 to 2.

In the formula (201), R⁵⁷ represents an aryl group which has 6 to 60carbon atoms and which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group which has 1 to 20 carbon atoms and which may have asubstituent, or an alkoxy group having 1 to 20 carbon atoms.

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In the formulae (202) and (203), R⁵⁸ and R⁵⁹ each independentlyrepresent a hydrogen atom, an aryl group which has 6 to 60 carbon atomsand which may have a substituent, a pyridyl group which may have asubstituent, a quinolyl group which may have a substituent, an alkylgroup which has 1 to 20 carbon atoms and which may have a substituent,or an alkoxy group which has 1 to 20 carbon atoms and which may have asubstituent.

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In the formulae (201) to (203), L⁷ represents a single bond, an arylenegroup which has 6 to 60 carbon atoms and which may have a substituent, apyridinylene group which may have a substituent, a quinolinylene groupwhich may have a substituent, or a fluorenylene group which may have asubstituent.

The arylene group which has 6 to 60 carbon atoms is preferably anarylene group having 6 to 40 carbon atoms, or more preferably an arylenegroup having 6 to 20 carbon atoms, and specific examples of such groupsinclude divalent groups each formed by removing one hydrogen atom fromthe aryl group described for R. Examples of the substituent of eachgroup represented by L⁷ include the same examples as those described forR⁵⁶.

In addition, L⁷ preferably represents a group selected from the groupconsisting of the following groups.

In the formula (201), Ar^(e) represents an arylene group which has 6 to60 carbon atoms and which may have a substituent, a pyridinylene groupwhich may have a substituent, or a quinolinylene group which may have asubstituent. Examples of the substituents of the respective groupsrepresented by Ar^(e) and Ar^(g) include the same examples as thosedescribed for R⁵⁶.

In addition, Ar^(e) preferably represents any one of the groups selectedfrom fused ring groups represented by the following formulae

In the formulae (101) to (110), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above.

In the formula (110), L′ represents a single bond or a group selectedfrom the group consisting of the following groups.

The formula (103) represented by Ar^(e) is preferably a fused ring grouprepresented by the following formulae (111) to (125).

In the formulae (111) to (125), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above.

In the formula (201), Ar^(f) represents a hydrogen atom, an aryl groupwhich has 6 to 60 carbon atoms and which may have a substituent, apyridyl group which may have a substituent, a quinolyl group which mayhave a substituent, an alkyl group which has 1 to 20 carbon atoms andwhich may have a substituent, or an alkoxy group which has 1 to 20carbon atoms and which may have a substituent.

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In the formulae (202) and (203), Ar^(g) represents an aryl group whichhas 6 to 60 carbon atoms and which may have a substituent, a pyridylgroup which may have a substituent, a quinolyl group which may have asubstituent, an alkyl group which has 1 to 20 carbon atoms and which mayhave a substituent, an alkoxy group which has 1 to 20 carbon atoms andwhich may have a substituent, or a group represented by —Ar^(e)—Ar^(f)(Ar^(e) and Ar^(e) each have the same meaning as that described above).

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In addition, Ar^(g) preferably represents any one of the groups selectedfrom fused ring groups represented by the following formulae (126) to(135).

In the formulae (126) to (135), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above.

In the formula (135), L′ is the same as that described above. In theformulae (126) to (135), R′ represents a hydrogen atom, an alkyl groupwhich has 1 to 20 carbon atoms and which may have a substituent, an arylgroup which has 6 to 40 carbon atoms and which may have a substituent,or a heteroaryl group which has 3 to 40 carbon atoms and which may havea substituent. Specific examples of the respective groups include thesame examples as those described above.

The general formula (128) represented by Ar^(g) is preferably a fusedring group represented by the following formulae (136) to (158).

In the formulae (136) to (158), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above. R′ is the same as that describedabove.

In addition, it is preferred that Ar^(f) and Ar^(g) each independentlyrepresent a group selected from the group consisting of the followinggroups.

Specific examples of the nitrogen-containing heterocyclic derivativesrepresented by the formulae (201) to (203) of the present invention areshown below. However, the present invention is not limited to theseexemplified compounds.

It should be noted that HAr in the following tables represent any one ofthe following parts in the formulae (201) to (203).

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 1-1

2

3

4

5

6

7

8

9

10

11

12

13

14

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 2-1

2

3

4

5

6

7

8

9

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 3-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 4-1

   2

   3

   4

   5

   6

   7

   8

   9

 10

 11

 12

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 5-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 6-1

2

3

4

5

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 7-1

2

3

4

5

6

7

8

9

10

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 8-1

2

3

4

5

6

7

8

9

10

11

12

13

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 9-1

2

3

4

5

6

7

8

9

10

11

12

13

14

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 10-1

2

3

4

5

6

7

8

9

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 11-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 12-1

2

3

4

6

7

8

9

10

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 13-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 14-1

2

3

4

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 15-1

2

3

4

5

6

7

8

9

10

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 16-1

2

3

4

5

6

7

8

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 17-1

2

3

4

5

6

8

Of those specific examples, (1-1), (1-5), (1-7), (2-1), (3-1), (4-2),(4-6), (7-2), (7-7), (7-8), (7-9), (9-1), and (9-7) are particularlypreferred.

In addition, as the nitrogen-containing ring derivative,nitrogen-containing five-membered ring derivative are also preferablyexemplified. Examples of the nitrogen-containing five-membered ringinclude an imidazole ring, a triazole ring, a tetrazole ring, anoxadiazole ring, a thiadiazole ring, an oxatriazole ring, and athiatriazole ring. Examples of the nitrogen-containing five-memberedring derivative include a benzoimidazole ring, a benzotriazole ring, apyridinoimidazole ring, a pyrimidinoimidazole ring, and apyridazinoimidazole ring. Particularly preferred is the compoundrepresented by the following general formula (B).

In the general formula (B), L^(B) represents a divalent or more bondinggroup. Examples thereof include a carbon atom, a silicon atom, anitrogen atom, a boron atom, an oxygen atom, a sulfur atom, metal atoms(for example, a barium atom, a beryllium atom), aromatic hydrocarbonrings, and aromatic heterocycles. Of those, preferred are a carbon atom,a nitrogen atom, a silicon atom, a boron atom, an oxygen atom, a sulfuratom, aromatic hydrocarbon rings, and aromatic heterocyclic groups, andmore preferred are a carbon atom, a silicon atom, aromatic hydrocarbonrings, and aromatic heterocyclic groups.

The aromatic hydrocarbon rings and aromatic heterocyclic groupsrepresented by L^(B) may have a substituent. Examples of the substituentinclude alkyl groups, alkenyl groups, aryl groups, amino groups, alkoxygroups, aryloxy groups, acyl groups, alkoxycarbonyl groups,aryloxycarbonyl groups, acyloxy groups, acylamino groups,alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfonylaminogroups, sulfamoyl groups, carbamoyl groups, alkylthio groups, arylthiogroups, sulfonyl groups, halogen atoms, cyano groups, and aromaticheterocyclic groups. Preferred are alkyl groups, aryl groups, alkoxygroups, aryloxy groups, halogen atoms, cyano groups, and aromaticheterocyclic groups, more preferred are alkyl groups, aryl groups,alkoxy groups, aryloxy groups, and aromatic heterocyclic groups, andparticularly preferred are alkyl groups, aryl groups, alkoxy groups, andaromatic heterocyclic groups.

Specific examples of L^(B) include compounds represented below.

X^(B2) in the general formula (B) represents —O—, —S—, or —N(R^(B2))—.R^(B2) represents a hydrogen atom, an aliphatic hydrocarbon group, anaryl group, or a heterocyclic group.

The aliphatic hydrocarbon group represented by R^(B2) is a linear orbranched alkyl group (having preferably 1 to 20, more preferably 1 to12, or particularly preferably 1 to 8 carbon atoms such as a methylgroup, an ethyl group, an isopropyl group, a t-butyl group, an n-octylgroup, an n-decyl group, or an n-hexadecyl group), a cycloalkyl group(having a ring formed of preferably 3 to 10 carbon atoms such as acyclopropyl group, a cyclopentyl group, or a cyclohexyl group), analkenyl group (having preferably 2 to 20, more preferably 2 to 12, orparticularly preferably 2 to 8 carbon atoms such as a vinyl group, anaryl group, a 2-butenyl group, or a 3-pentenyl group), or an alkynylgroup (having preferably 2 to 20, more preferably 2 to 12, orparticularly preferably 2 to 8 carbon atoms such as a propargyl group ora 3-pentynyl group), or is preferably an alkyl group.

The aryl group represented by R^(B2) is a monocycle or a fused ring, andis an aryl group having a ring formed of preferably 6 to 30, morepreferably 6 to 20, or still more preferably 6 to 12 carbon atoms.Examples of such groups include a phenyl group, a 2-methylphenyl group,a 3-methylphenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group,a 3-trifluoromethylphenyl group, a pentafluorophenyl group, a 1-naphthylgroup, and a 2-naphthyl group. Of those, a phenyl group or a2-methylphenyl group is preferable.

The heterocyclic group represented by R^(B2) is a monocycle or a fusedring, and is a heterocyclic group having a ring formed of preferably 1to 20, more preferably 1 to 12, or still more preferably 2 to 10 carbonatoms. The heterocyclic group is an aromatic heterocyclic groupcontaining at least one heteroatom selected from a nitrogen atom, anoxygen atom, a sulfur atom, and a selenium atom. Examples of theheterocyclic group include groups derived from pyrrolidine, piperidine,piperazine, morpholine, thiophene, selenophene, furan, pyrrole,imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine,triazole, triazine, indole, indazole, purine, thiazoline, thiazole,thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline,phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline,pteridine, acridine, phenanthroline, phanazine, tetrazole,benzoimidazole, benzoxazole, benzothiazole, benzotriazole,tetrazaindene, carbazole, azepine, and the like. Preferred are groupsderived from furan, thiophene, pyridine, pyrazine, pyrimidine,pyridazine, triazine, quinoline, phthalazine, naphthyridine,quinoxaline, and quinazoline, more preferred are groups derived fromfuran, thiophene, pyridine, and quinoline, and still more preferred is aquinolinyl group.

The aliphatic hydrocarbon group, the aryl group, and the heterocyclicgroup each represented by R^(B2) may each have a substituent, and thesubstituent is preferably an alkyl group, an alkenyl group, an alkynylgroup, an aryl group, an amino group, an alkoxy group, an aryloxy group,an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, anacyloxy group, an acylamino group, an alkoxycarbonylamino group, anaryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, acarbamoyl group, an alkylthio group, an arylthio group, a sulfonylgroup, a halogen atom, a cyano group, or an aromatic heterocyclic group,more preferably an alkyl group, an aryl group, an alkoxy group, anaryloxy group, a halogen atom, a cyano group, or an aromaticheterocyclic group, still more preferably an alkyl group, an aryl group,an alkoxy group, an aryloxy group, or an aromatic heterocyclic group, orparticularly preferably an alkyl group, an aryl group, an alkoxy group,or an aromatic heterocyclic group.

R^(B2) preferably represents an aliphatic hydrocarbon group, an arylgroup, or a heterocyclic group, more preferably represents an aliphatichydrocarbon group (having preferably € to 30, more preferably 6 to 20,or still more preferably 6 to 12 carbon atoms) or an aryl group, orstill more preferably represents an aliphatic hydrocarbon group (havingpreferably 1 to 20, more preferably 1 to 12, or still more preferably 2to 10 carbon atoms).

X^(B2) preferably represents —O— or —N(R^(B2))—, or more preferablyrepresents —N(R^(B2))—.

Z^(B2) represents atoms necessary for forming an aromatic ring. Thearomatic ring formed of Z^(B2) is any one of aromatic hydrocarbon ringsand aromatic heterocyclic rings. Specific examples thereof include abenzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, apyridazine ring, a triazine ring, a pyrrole ring, a furan ring, athiophene ring, a selenophene ring, a tellurophene ring, an imidazolering, a thiazole ring, a selenazole ring, a tellulazole ring, athiadiazole ring, an oxadiazole ring, and a pyrazole ring. Preferred area benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, anda pyridazine ring, more preferred are a benzene ring, a pyridine ring,and a pyrazine ring, still more preferred are a benzene ring and apyridine ring, and particularly preferred is a pyridine ring.

The aromatic ring formed of Z^(B2) may further form a fused ring withany other rings, or may have a substituent. Examples of the substituentinclude the same examples as those described for the substituent of thegroup represented by L^(B), and the substituent is preferably an alkylgroup, an alkenyl group, an alkynyl group, an aryl group, an aminogroup, an alkoxy group, an aryloxy group, an acyl group, analkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, anacylamino group, an alkoxycarbonylamino group, an aryloxycarbonylaminogroup, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, analkylthio group, an arylthio group, a sulfonyl group, a halogen atom, acyano group, or a heterocyclic group, more preferably an alkyl group, anaryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyanogroup, or a heterocyclic group, still more preferably an alkyl group, anaryl group, an alkoxy group, an aryloxy group, or an aromaticheterocyclic group, or particularly preferably an alkyl group, an arylgroup, an alkoxy group, or an aromatic heterocyclic group.

n^(B2) represents an integer of 1 to 4, or preferably 2 or 3.

Of the nitrogen-containing five-membered ring derivatives eachrepresented by the general formula (B), a derivative represented by thefollowing general formula (B′) is more preferable.

In the general formula (B′), R^(B71), R^(B72), and R^(B73) each have thesame meaning as that of R^(B2) in the general formula (B), and thepreferable ranges of R^(B71), R^(B72), and R^(B73) are also the same asthose of R^(B2).

In the formula, Z^(B71), Z^(B72), and Z^(B73) each have the same meaningas that of Z^(B2) in the general formula (B), and the preferable rangesof Z^(B71), Z^(B72), and Z^(B73) are also the same as those of Z^(B2).

In the formula, L^(B71), L^(B72), and L^(B73) each represent a linkinggroup, and examples of the linking group include examples obtained bymaking the examples of L^(B) in the general formula (B) divalent. Thelinking group is preferably a single bond, a divalent aromatichydrocarbon ring group, a divalent aromatic heterocyclic group, or alinking group composed of a combination of two or more of them, or ismore preferably a single bond. L^(B71), L^(B72), and L^(B73) may eachhave a substituent. Examples of the substituent include the sameexamples as those described for the substituent of the group representedby L^(B) in the general formula (B), and preferable examples of thesubstituent also include the same preferable examples as those describedfor the substituent of the group represented by L^(B) in the generalformula (B).

In the formula, Y^(B) represents a nitrogen atom, a 1,3,5-benzenetriylgroup, or a 2,4,6-triazinetriyl group. The 1,3,5-benzenetriyl group mayhave a substituent at any one of its 2-, 4-, and 6-positions, andexamples of the substituent include an alkyl group, an aromatichydrocarbon ring group, and a halogen atom.

Specific examples of the nitrogen-containing five-membered ringderivative represented by the general formula (B) or (B′) are shownbelow. However, the present invention is not limited to theseexemplified compounds.

A compound of which each of the electron injecting layer and theelectron transporting layer is constituted is, for example, a compoundhaving a structure obtained by combining an electron-deficient,nitrogen-containing five-membered ring skeleton or electron-deficient,nitrogen-containing six-membered ring skeleton and a substituted orunsubstituted indole skeleton, substituted or unsubstituted carbazoleskeleton, or substituted or unsubstituted azacarbazole skeleton as wellas the material for an organic EL device of the present invention. Inaddition, a suitable electron-deficient, nitrogen-containingfive-membered ring skeleton or electron-deficient, nitrogen-containingsix-membered ring skeleton is a molecular skeleton such as a pyridine,pyrimidine, pyrazine, triazine, triazole, oxadiazole, pyrazole,imidazole, quinoxaline, or pyrrole skeleton, or benzimidazole orimidazopyridine obtained when two or more of them fuse with each other.Of those combinations, a preferable combination is, for example, acombination of a pyridine, pyrimidine, pyrazine, or triazine skeletonand a carbazole, indole, azacarbazole, or quinoxaline skeleton. Theabove-mentioned skeleton may be substituted or unsubstituted.

Specific examples of an electron transportable compound are shown below.However, the present invention is not particularly limited to theseexamples.

Each of the electron injecting layer and the electron transporting layermay be of a monolayer structure composed of one or two or more kinds ofthe above materials, or may be of a multi-layered structure composed ofmultiple layers identical to or different from each other incomposition. Materials for those layers each preferably have an-electron-deficient, nitrogen-containing heterocyclic group.

In addition, an insulator or semiconductor serving as an inorganiccompound as well as the nitrogen-containing ring derivative ispreferably used as a component of the electron injecting layer. When theelectron injecting layer is constituted of an insulator orsemiconductor, current leakage can be effectively prevented, and theelectron injecting property of the layer can be improved.

As the insulator, at least one metal compound selected from the groupconsisting of alkali metal chalcogenides, alkaline earth metalchalcogenides, alkali metal halides, and alkaline earth metal halides ispreferably used. It is preferable that the electron injecting layer becomposed of the above-mentioned substance such as the alkali metalchalcogenide since the electron injecting property can be furtherimproved. To be specific, preferable examples of the alkali metalchalcogenide include Li₂O, K₂O, Na₂S, Na₂Se, and Na₂O, and preferableexamples of the alkaline earth metal chalcogenide include CaO, BaO, SrO,BeO, BaS, and CaSe. Preferable examples of the alkali metal halideinclude LiF, NaF, KF, LiCl, KCl, and NaCl. Preferable examples of thealkaline earth metal halide include fluorides such as CaF₂, BaF₂, SrF₂,MgF₂, and BeF₂ and halides other than the fluorides.

In addition, examples of the semiconductor include oxides, nitrides, andoxide nitrides containing at least one element selected from the groupconsisting of Ba, Ca, Sr, Yb, Al, Ga, In, L₁, Na, Cd, Mg, Si, Ta, Sb,and Zn, and they may be used alone or in combination of two or more. Itis preferable that the inorganic compound composing the electroninjecting layer form a crystallite or amorphous insulating thin film.When the electron injecting layer is composed of the insulating thinfilm described above, a more uniform thin film can be formed, anddefects of pixels such as dark spots can be decreased. Examples of theinorganic compound include alkali metal chalcogenides, alkaline earthmetal chalcogenides, alkali metal halides, and alkaline earth metalhalides.

In addition, the above-mentioned reducing dopant can be preferablyincorporated into the electron injecting layer in the present invention.

It should be noted that the thickness of each of the electron injectinglayer and the electron transporting layer, which is not particularlylimited, is preferably 1 to 100 nm.

An aromatic amine compound such as an aromatic amine derivativerepresented by a general formula (I) is suitably used in the holeinjecting layer or hole transporting layer (a holeinjecting/transporting layer is also included in this category).

In the general formula (I), Ar¹ to Ar⁴ each represent a substituted orunsubstituted aryl group having a ring formed of 6 to 50 carbon atoms,or a substituted or unsubstituted heteroaryl group having a ring formedof 5 to 50 atoms.

Examples of the substituted or unsubstituted aryl group having a ringformed of 6 to 50 carbon atoms include a phenyl group, a 1-naphthylgroup, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, anm-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-ylgroup, an o-tolyl group, an m-tolyl group, a p-tolyl group, ap-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, a4″-t-butyl-p-terphenyl-4-yl group, a fluoranthenyl group, and afluorenyl group.

Examples of the substituted or unsubstituted heteroaryl group having aring formed of 5 to 50 atoms include a 1-pyrrolyl group, a 2-pyrrolylgroup, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolylgroup, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolylgroup, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group,a 6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group,a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl1-indolyl group, a 4-t-butyl1-indolyl group, a2-t-butyl3-indolyl group, and a 4-t-butyl3-indolyl group. Preferred area phenyl group, a naphthyl group, a biphenyl group, an anthranyl group,a phenanthryl group, a pyrenyl group, a chrycenyl group, a fluoranthenylgroup, and a fluorenyl group.

L represents a linking group, and specifically, a substituted orunsubstituted arylene group having a ring formed of 6 to 50 carbonatoms, a substituted or unsubstituted heteroarylene group having a ringformed of 5 to 50 atoms, or a divalent group in which two or morearylene groups or heteroarylene groups are bonded by a single bond, anether bond, a thioether bond, with an alkylene group having 1 to 20carbon atoms, an alkenylene group having 2 to 20 carbon atoms, and anamino group. Examples of the arylene group having a ring formed of 6 to50 carbon atoms include a 1,4-phenylene group, a 1,2-phenylene group, a1,3-phenylene group, a 1,4-naphthylene group, a 2,6-naphthylene group, a1,5-naphthylene group, a 9,10-anthranylene group, a9,10-phenanthrenylene group, a 3,6-phenanthrenylene group,1,6-pyrenylene group, a 2,7-pyrenylene group, a 6,12-chrycenylene group,a 4,4′-biphenylene group, a 3,3′-biphenylene group, a 2,2′-biphenylenegroup, and a 2,7-fluorenylene group. Examples of the arylene grouphaving a ring formed of 5 to 50 atoms include a 2,5-thiophenylene group,a 2,5-silolylene group, and a 2,5-oxadiazolylene group. Preferred are a1,4-phenylene group, a 1,2-phenylene group, a 1,3-phenylene group, a1,4-naphthylene group, a 9,10-anthranylene group, a 6,12-chrysenylenegroup, a 4,4′-biphenylene group, a 3,3′-biphenlene group, a2,2′-biphenylene group, and a 2,7-fluorenylene group.

In the case where L represents a linking group formed of two or morearylene groups or heteroarylene groups, adjacent arylene groups orheteroarylene groups may be bonded to each other through a divalentgroup to form a ring. Examples of the divalent group forming a ringinclude a tetramethylene group, a pentamethylene group, a hexamethylenegroup, a diphenylmethane-2,2′-diyl group, a diphenyl ethane-3,3′-diylgroup, and a diphenylpropane-4,4′-diyl group.

The substituent of each of Ar¹ to Ar⁴ and L is, for example, asubstituted or unsubstituted aryl group having a ring formed of 6 to 50carbon atoms, a substituted or unsubstituted heteroaryl group having aring formed of 5 to 50 atoms, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkylgroup having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 50 carbon atoms, a substituted or unsubstitutedaralkyl group having 7 to 50 carbon atoms, a substituted orunsubstituted aryloxy group having a ring formed of 6 to 50 carbonatoms, a substituted or unsubstituted heteroaryloxy group having a ringformed of 5 to 50 atoms, a substituted or unsubstituted arylthio grouphaving a ring formed of 6 to 50 carbon atoms, a substituted orunsubstituted heteroaryl thio group having a ring formed of 5 to 50atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to50 carbon atoms, an amino group substituted by a substituted orunsubstituted aryl group having a ring formed of 6 to 50 carbon atoms orby a substituted or unsubstituted heteroaryl group having a ring formedof 5 to 50 atoms, a halogen group, a cyano group, a nitro group, or ahydroxyl group.

Examples of the substituted or unsubstituted aryl group having a ringformed of 6 to 50 carbon atoms include a phenyl group, a 1-naphthylgroup, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, anm-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-ylgroup, an o-tolyl group, an m-tolyl group, a p-tolyl group, ap-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, a4″-t-butyl-p-terphenyl-4-yl group, a fluoranthenyl group, and afluorenyl group.

Examples of the substituted or unsubstituted heteroaryl group having aring formed of 5 to 50 atoms include a 1-pyrrolyl group, a 2-pyrrolylgroup, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolylgroup, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolylgroup, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group,a 6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group,a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl1-indolyl group, a 4-t-butyl1-indolyl group, a2-t-butyl3-indolyl group, and a 4-t-butyl3-indolyl group.

Examples of the substituted or unsubstituted alkyl group having 1 to 50carbon atoms include a methyl group, an ethyl group, a propyl group, anisopropyl group, an n-butyl group, an s-butyl group, an isobutyl group,a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group,an n-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted cycloalkyl group having 3to 50 carbon atoms include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a2-norbornyl group.

The substituted or unsubstituted alkoxy group having 1 to 50 carbonatoms is a group represented by —OY. Examples of Y include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted aralkyl group having 7 to50 carbon atoms include a benzyl group, a 1-phenylethyl group, a2˜phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropylgroup, a phenyl-t-butyl group, an α-naphthylmethyl group, a1-α-naphthylethyl group, a 2-α-naphthylethyl group; a1-α-naphthylisopropyl group, a 2-α-naphthyl isopropyl group, aβ-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, a1-pyrolylmethyl group, a 2-(1-pyrrolyl)ethyl group, a p-methylbenzylgroup, an m-methylbenzyl group, an o-methylbenzyl group, ap-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzyl group,a p-bromobenzyl group, an m-bromobenzyl group, an o-bromobenzyl group, ap-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, ap-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzylgroup, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzylgroup, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzylgroup, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzylgroup, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group.

Examples of the substituted or unsubstituted aryloxy group having a ringformed of 6 to 50 carbon atoms is represented by —OY′. Examples of Y′include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthrylgroup, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthrylgroup, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenylgroup, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a4-pyrenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group,a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-ylgroup, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, ap-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenylgroup, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group.

Examples of the substituted or unsubstituted heteroaryloxy group havinga ring formed of 5 to 50 atoms is represented by —OZ′. Examples of Z′include a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 2-indolylgroup, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 3-isoindolylgroup, a 4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group,a 7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 1-phenanthridinyl group, a 2-phenanthridinyl group, a3-phenanthridinyl group, a 4-phenanthridinyl group, a 6-phenanthridinylgroup, a 7-phenanthridinyl group, an 8-phenanthridinyl group, a9-phenanthridinyl group, a 10-phenanthridinyl group, a 1-acridinylgroup, a 2-acridinyl group, a 3-acridinyl group, a 4-acridinyl group, a9-acridinyl group, a 1,7-phenanthrolin-2-yl group, a1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxadinylgroup, a 2-phenoxadinyl group, a 3-phenoxadinyl group, a 4-phenoxadinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl) pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a4-t-butyl1-indolyl group, a 2-t-butyl3-indolyl group, and a4-t-butyl3-indolyl group.

The substituted or unsubstituted arylthio group having a ring formed of6 to 50 carbon atoms is represented by —SY″. Examples of Y″ include aphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group,a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group.

The substituted or unsubstituted heteroarylthio group having a ringformed of 5 to 50 atoms is represented by —SZ″. Examples of Z″ include a2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinylgroup, a 3-pyridinyl group, a 4-pyridinyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 3-isoindolyl group, a4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 1-phenanthridinyl group, a 2-phenanthridinyl group, a3-phenanthridinyl group, a 4-phenanthridinyl group, a 6-phenanthridinylgroup, a 7-phenanthridinyl group, an 8-phenanthridinyl group, a9-phenanthridinyl group, a 10-phenanthridinyl group, a 1-acridinylgroup, a 2-acridinyl group, a 3-acridinyl group, a 4-acridinyl group, a9-acridinyl group, a 1,7-phenanthrolin-2-yl group, a1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxazinylgroup, a 2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a4-t-butyl1-indolyl group, a 2-t-butyl3-indolyl group, and a4-t-butyl3-indolyl group.

The substituted or unsubstituted alkoxycarbonyl group having 2 to 50carbon atoms is represented by —COOZ. Examples of Z include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroispropyl group, a2,3-dinitro-t-butyl group, and 1,2,3-trinitropropyl group.

The substituted or unsubstituted aryl group having a ring formed of 6 to50 carbon atoms or an amino group substituted with a substituted orunsubstituted heteroaryl group having a ring formed of 5 to 50 atoms isrepresented by —NPQ. Examples of P and Q include a phenyl group, a1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthrylgroup, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group,a 3-phenanthryl group, 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, anm-terphenyl-4-yl group, a an m-terphenyl-3-yl group, an m-terphenyl-2-ylgroup, an o-tolyl group, an m-tolyl group, a p-tolyl group, ap-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group, a 2-pyrrolyl group, a 3-pyrrolylgroup, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a4-pyridinyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolylgroup, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, a1-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a5-isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a2-furyl group, a 3-furyl group, a 2-benzofuranyl group, a 3-benzofuranylgroup, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranylgroup, a 7-benzofuranyl group, a 1-isobenzofuranyl group, a3-isobenzofuranyl group, a 4-isobenzofuranyl group, a 5-isobenzofuranylgroup, a 6-isobenzofuranyl group, a 7-isobenzofuranyl group, a2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolylgroup, a 6-quinolyl group, a 7-quinolyl group, an 8-quinolyl group, a1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, an8-isoquinolyl group, a 2-quinoxalinyl group, a 5-quinoxalinyl group, a6-quinoxalinyl group, a 1-carbazolyl group, a 2-carbazolyl group, a3-carbazolyl group, a 4-carbazolyl group, a 1-phenanthridinyl group, a2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinylgroup, a 6-phenanthridinyl group, a 7-phenanthridinyl group, an8-phenanthridinyl group, a 9-phenanthridinyl group, a 10-phenanthridinylgroup, a 1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group,4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxazinylgroup, a 2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a4-t-butyl1-indolyl group, a 2-t-butyl3-indolyl group, and a4-t-butyl3-indolyl group.

Specific examples of the compound represented by the general formula (I)are shown below. However, the present invention is not limited to theseexamples.

In addition, an aromatic amine represented by the following generalformula (II) is also suitably used in the formation of the holeinjecting layer or hole transporting layer.

In the general formula (II), the definition of Ar₁ to Ar₃ is the same asthat of Ar₁ to Ar₄ in the general formula (I). Specific examples of thecompound represented by the general formula (II) are shown below.However, the present invention is not limited to these examples.

The compound of the present invention can be used in each of the holeinjecting layer, the hole transporting layer, the electron injectinglayer, and the electron transporting layer because the compound cantransport both a hole and an electron.

In the present invention, the anode in the organic EL device has thefunction of injecting holes into the hole transporting layer or thelight emitting layer. It is effective that the anode has a work functionof 4.5 eV or greater. Specific examples of the material for the anodeused in the present invention include indium tin oxide alloys (ITO), tinoxide (NESA), gold, silver, platinum, and copper. In addition, as thecathode, a material having a small work function is preferred in view toinject an electron into an electron injecting layer or a light emittinglayer. Examples of the cathode material are not particularly limited,and specifically, indium, aluminum, magnesium, an magnesium-indiumalloy, a magnesium-aluminum alloy, an aluminum-lithium alloy, analuminum-scandium-lithium alloy, and a magnesium-silver alloy may beused.

The method of forming the layers in the organic EL device of the presentinvention is not particularly limited. A conventionally known processsuch as the vacuum vapor deposition process or the spin coating processcan be used. The organic thin film layer which is used in the organic ELdevice of the present invention and includes the compound represented bygeneral formula (1) described above can be formed in accordance with aknown process such as the vacuum vapor deposition process or themolecular beam epitaxy process (MBE process) or, using a solutionprepared by dissolving the compounds into a solvent, in accordance witha coating process such as the dipping process, the spin coating process,the casting process, the bar coating process, or the roll coatingprocess.

The thickness of each organic layer in the organic EL device of thepresent invention is not particularly limited. In general, anexcessively thin layer tends to have defects such as pin holes, whereasan excessively thick layer requires a high applied voltage to decreasethe efficiency. Therefore, a thickness in the range of severalnanometers to 1 μm is preferable.

EXAMPLES

Next, the present invention is described in detail by way of examples,but the present invention is not limited to the following examples. Notethat, in the synthesis examples below, DMF refers to dimethylformamide,THF refers to tetrahydrofuran, DME refers to dimethoxyethane, NBS refersto N-bromosuccine imide, Ph refers to a phenyl group, AcOEt refers toethyl acetate, and NMP refers to N-methyl pyrrolidone.

Synthesis Example 1 (Synthesis of Compound No. 11)

Compound 1 (2.6 g, 10 mmol), 2-bromobenzofuran (5.0 g, 20 mmol), CuI(1.9 g, 10 mmol), transcyclohexane 1,2-diamine (3.4 g, 30 mmol), K₃PO₄(8.5 g, 40 mmol), and 1,4-dioxane (10 mL) were loaded into athree-necked flask, and the mixture was refluxed under an argonatmosphere for 10 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The resultant sample was purified by silicagel column chromatography. The purified product was concentrated andexsiccated, and was then recrystallized twice, whereby a white powder(Compound No. 11) was obtained. The powder was purified by sublimation,whereby a white solid was obtained in an amount of 0.7 g in 12% yield.

FD-MS C₄₂H₂₄N₂O₂: theoretical value 588, observed value 588

Synthesis Example 2 (Synthesis of Compound No. 40)

Compound 2 (2.6 g, 10 mmol), 2-bromobenzofuran (5.0 g, 20 mmol), CuI(1.9 g, 10 mmol), transcyclohexane 1,2-diamine (3.4 g, 30 mmol), K₃PO₄(8.5 g, 40 mmol), and 1,4-dioxane (10 mL) were loaded into athree-necked flask, and the mixture was refluxed under an argonatmosphere for 10 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The resultant sample was purified by silicagel column chromatography. The purified product was concentrated andexsiccated, and was then recrystallized twice, whereby a white powder(Compound No. 40) was obtained. The powder was purified by sublimation,whereby a white solid was obtained in an amount of 1.9 g in 33% yield.

FD-MS C₄₂H₂₄N₂O₂: theoretical value 588, observed value 588

Synthesis Example 3 (Synthesis of Compound No. 47)

Compound 3 (2.6 g, 10 mmol), 2-bromobenzofuran (5.0 g, 20 mmol), CuI(1.9 g, 10 mmol), transcyclohexane 1,2-diamine (3.4 g, 30 mmol), K₃PO₄(8.5 g, 40 mmol), and 1,4-dioxane (10 mL) were loaded into athree-necked flask, and the mixture was refluxed under an argonatmosphere for 10 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The resultant sample was purified by silicagel column chromatography. The purified product was concentrated andexsiccated, and was then recrystallized twice, whereby a white powder(Compound No. 47) was obtained. The powder was purified by sublimation,whereby a white solid was obtained in an amount of 1.5 g in 25% yield.

FD-MS C₄₂H₂₄N₂O₂: theoretical value 588, observed value 588

Synthesis Example 4 (Synthesis of Compound No. 66)

Compound 4 (2.6 g, 10 mmol), 2-bromobenzofuran (5.0 g, 20 mmol), CuI(1.9 g, 10 mmol), transcyclohexane 1,2-diamine (3.4 g, 30 mmol), K₃PO₄(8.5 g, 40 mmol), and 1,4-dioxane (10 mL) were loaded into athree-necked flask, and the mixture was refluxed under an argonatmosphere for 10 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The resultant sample was purified by silicagel column chromatography. The purified product was concentrated andexsiccated, and was then recrystallized twice, whereby a white powder(Compound No. 66) was obtained. The powder was purified by sublimation,whereby a white solid was obtained in an amount of 2.4 g in 40% yield.

FD-MS C₄₂H₂₄N₂O₂: theoretical value 588, observed value 588

Synthesis Example 5 (Synthesis of Compound No. 100)

(1) Synthesis of Compound 5

1,2-difluoro-3,6-diiodobenzene (65.9 g, 180.0 mmol),2-methoxyphenylboronic acid (65.6 g, 432.0 mmol), a 2 M aqueous solutionof Na₂CO₃ (360 mL, 720 mmol), DME (360 mL), toluene (360 mL), andPd[PPh₃]₄ (20.8 g, 18.0 mmol) were loaded into a three-necked flask, andthe mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (500 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 38.2 g in 65% yield. FD-MS C₂₀H₁₆F₂O₂: theoretical value326, observed value 326

(2) Synthesis of Compound 6

Compound 5 (38.0 g, 116.4 mmol), NBS (41.5 g, 232.9 mmol), and DMF(1,000 mL) were loaded into a three-necked flask, and the mixture wasstirred under an Ar atmosphere at room temperature for 8 hours. Afterthe completion of the reaction, the resultant sample was transferred toa separating funnel, and water (1,000 mL) was charged into the funnel.Then, the mixture was extracted with AcOEt. The resultant sample waspurified by column chromatography, whereby a white solid was obtained inan amount of 45.1 g in 80% yield.

FD-MS C₂₀H₁₄Br₂F₂O₂: theoretical value 484, observed value 484

(3) Synthesis of Compound 7

Compound 6 (45.0 g, 93.0 mmol), a 1 M solution of BBr₃ in CH₂Cl₂ (218mL, 218 mmol), and CH₂Cl₂ (560 mL) were loaded into a three-neckedflask, and the mixture was stirred under an Ar atmosphere at 0° C. for 8hours. After that, the mixture was left to stand at room temperatureovernight. After the completion of the reaction, the resultant wasneutralized with a saturated aqueous solution of NaHCO₃. The resultantsample was transferred to a separating funnel, and was extracted withCH₂Cl₂. The resultant sample was purified by column chromatography,whereby a white solid was obtained in an amount of 35.2 g in 83% yield.

FD-MS C₁₈H₁₀Br₂F₂O₂: theoretical value 456, observed value 456

(4) Synthesis of Compound 8

Compound 7 (35.0 g, 76.7 mmol), K₂CO₃ (23.3 g, 168.8 mmol), and NMP (320mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at 150° C. for 8 hours. After the completion ofthe reaction, the resultant was cooled to room temperature. Theresultant sample was transferred to a separating funnel, and water (500mL) was charged into the funnel. Then, the mixture was extracted withAcOEt. The resultant sample was purified by column chromatography,whereby a white solid was obtained in an amount of 27.1 g in 85% yield.

FD-MS C₁₈H₈Br₂O₂: theoretical value 416, observed value 416

(5) Synthesis of Compound No. 100

Compound 8 (2.5 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 100) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.0 g in45% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 6 (Synthesis of Compound No. 103)

(1) Synthesis of Compound 10

Compound 8 (16.8 g, 40 mmol), phenylboronic acid (4.8 g, 40 mmol), a 2 Maqueous solution of Na₂CO₃ (80 ml, 160 mmol), DME (80 mL), toluene (80mL), and Pd[PPh₃]₄ (2.3 g, 2.0 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (150 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 12.4 g in 75% yield.

FD-MS C₂₄H₁₃BrO₂: theoretical value 413, observed value 413

(2) Synthesis of Compound 11

Compound 10 (12.0 g, 29.0 mmol) and THF (288 mL) were loaded into athree-necked flask, and the mixture was, cooled to −78° C. Then, n-BuLi(1.65 M solution in n-hexane, 19.4 mL, 31.9 mmol) was added dropwise tothe flask, and the resultant mixture was stirred at −78° C. for 20minutes. Triisopropyl borate (16.4 g, 87.0 mmol) was added to theresultant, and the mixture was stirred at −78° C. for 1 hour. Afterthat, the resultant was left to stand overnight at room temperature.Then, 1 N HCl (100 mL) was charged into the resultant, and the mixturewas stirred at room temperature for 1 hour. The resultant sample wasconcentrated, and was then transferred to a separating funnel. Water(100 mL) was charged into the funnel, and the mixture was extracted withCH₂Cl₂. The extract was dried with MgSO₄, and was then filtrated andconcentrated. The resultant sample was purified by recrystallization(toluene-hexane), whereby a white solid was obtained in an amount of 7.1g in 65% yield.

(3) Synthesis of Compound No. 103

Compound 11 (5.5 g, 14.5 mmol), 1,3-dibromobenzene (1-7 g, 7.3 mmol), a2 M aqueous solution of Na₂CO₃ (15 mL, 30 mmol), DME (15 mL), toluene(15 mL), and Pd[PPh₃]₄ (0.42 g, 0.37 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 103) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.4 g in45% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 7 (Synthesis of Compound No. 116)

(1) Synthesis of Compound 12

1,3-dibromo-4,6-difluorobenzene (50.0 g, 183.9 mmol),2-methoxyphenylboronic acid (67.1 g, 441.1 mmol), and a 2 M aqueoussolution of Na₂CO₃ (368 mL, 736 mmol), DME (370 mL), toluene (370 mL),and Pd[PPh₃]₄ (21 g, 18.0 mmol) were loaded into a three-necked flask,and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (500 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 40.2 g in 67% yield.

FD-MS C₂₀H₁₆F₂O₂: theoretical value 326, observed value 326

(2) Synthesis of Compound 13

Compound 12 (40.0 g, 122.6 mmol), NBS (43.6 g, 245 mmol), and DMF (1,000mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at room temperature for 8 hours. After thecompletion of the reaction, the resultant sample was transferred to aseparating funnel, and water (1,000 mL) was charged into the funnel.Then, the mixture was extracted with AcOEt. The resultant sample waspurified by column chromatography, whereby a white solid was obtained inan amount of 42.1 g in 71% yield.

FD-MS C₂₀H₁₄Br₂F₂O₂: theoretical value 484, observed value 484

(3) Synthesis of Compound 14

Compound 13 (40.0 g, 82.6 mmol), a 1 M solution of BBr₂ in CH₂Cl₂ (194mL, 194 mmol), and CH₂Cl₂ (500 mL) were loaded into a three-neckedflask, and the mixture was stirred under an Ar atmosphere at 0° C. for 8hours. After that, the mixture was left to stand at room temperatureovernight. After the completion of the reaction, the resultant wasneutralized with a saturated aqueous solution of NaHCO₃. The resultantsample was transferred to a separating funnel, and was extracted withCH₂Cl₂. The resultant sample was purified by column chromatography,whereby a white solid was obtained in an amount of 30.2 g in 80% yield.

FD-MS C₁₈H₁₀Br₂F₂O₂: theoretical value 456, observed value 456

(4) Synthesis of Compound 15

Compound 14 (30.0 g, 65.7 mmol), K₂CO₃ (19.9 g, 144.5 mmol), and NMP(270 mL) were loaded into a three-necked flask, and the mixture wasstirred under an Ar atmosphere at 150° C. for 8 hours. After thecompletion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (500 mL) was charged into the funnel. Then, themixture was extracted with AcOEt. The resultant sample was purified bycolumn chromatography, whereby a white solid was obtained in an amountof 21.9 g in 80% yield.

FD-MS C₁₈H₈Br₂O₂: theoretical value 416, observed value 416

Compound 15 (2.5 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 116) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.7 g in60% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 8 (Synthesis of Compound No. 119)

(1) Synthesis of Compound 16

Confound 15 (16.8 g, 40 mmol), phenylboronic acid (4.8 g, 40 mmol), a 2M aqueous solution of Na₂CO₃ (80 mL, 160 mmol), DME (80 mL), toluene (80mL), and Pd[PPh₃]₄ (2.3 g, 2.0 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (150 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 11.6 g in 70% yield.

FD-MS C₂₄H₁₃BrO₂: theoretical value 413, observed value 413

(2) Synthesis of Compound 17

Compound 16 (11.0 g, 26.6 mmol) and THF (264 mL) were loaded into athree-necked flask, and the mixture was cooled to −78° C. Then, n-BuLi(1.65 M solution in n-hexane, 17.7 mL, 29.3 mmol) was added dropwise tothe flask, and the resultant mixture was stirred at −78° C. for 20minutes. Triisopropyl borate (15.1 g, 80 mmol) was added to theresultant, and the mixture was stirred at −78° C. for 1 hour. Afterthat, the resultant was left to stand overnight at room temperature.Then, 1 N HCl (100 mL) was charged into the resultant, and the mixturewas stirred at room temperature for 1 hour. The resultant sample wasconcentrated, and was then transferred to a separating funnel. Water(100 mL) was charged into the funnel, and the mixture was extracted withCH₂Cl₂. The extract was dried with MgSO₄, and was then filtrated andconcentrated. The resultant sample was purified by recrystallization(toluene-hexane), whereby a white solid was obtained in an amount of 6.1g in 61% yield.

(3) Synthesis of Compound No. 119

Compound 17 (5.5 g, 14.5 mmol), 1,3-dibromobenzene (1.7 g, 7.3 mmol), a2 M aqueous solution of Na₂CO₃ (15 mL, 30 mmol), DME (15 mL), toluene(15 mL), and Pd[PPh₃]₄ (0.42 g, 0.37 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 119) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.9 g in35% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 9 (Synthesis of Compound No. 134)

Compound 18 (2.5 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 134) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.8 g in41% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 10 (Synthesis of Compound No. 139)

Confound 19 (5.0 g, 13.2 mmol), 1,3-dibromobenzene (1.5 g, 6.6 mmol), a2 M aqueous solution of Na₂CO₃ (14 mL, 28 mmol), DME (14 mL), toluene(14 mL), and Pd[PPh₃]₄ (0.38 g, 0.34 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 139) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.9 g in39% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 11 (Synthesis of Compound No. 154)

(1) Synthesis of Compound 20

1,2-dibromo-3,6-difluorobenzene (50.0 g, 183.9 mmol),2-methoxyphenylboronic acid (67.1 g, 441.4 mmol), and a 2 M aqueoussolution of Na₂CO₃ (368 mL, 736 mmol), DME (370 mL), toluene (370 mL),and Pd[PPh₃]₄ (21.3 g, 18.4 mmol) were loaded into a three-necked flask,and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (500 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 30.6 g in 51% yield.

FD-MS C₂₀H₁₆F₂O₂: theoretical value 326, observed value 326

(2) Synthesis of Compound 21

Compound 20 (30.0 g, 91.9 mmol), NBS (32.8 g, 184 mmol), and DMF (820mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at room temperature for 8 hours. After thecompletion of the reaction, the resultant sample was transferred to aseparating funnel, and water (1,000 mL) was charged into the funnel.Then, the mixture was extracted with AcOEt. The resultant sample waspurified by column chromatography, whereby a white solid was obtained inan amount of 32 g in 72% yield.

FD-MS C₂₀H₁₄Br₂F₂O₂: theoretical value 484, observed value 484

(3) Synthesis of Compound 22

Compound 21 (32.0 g, 66.1 mmol), a 1 M solution of BBr₃ in CH₂Cl₂ (155mL, 155 mmol), and CH₂Cl₂ (430 mL) were loaded into a three-neckedflask, and the mixture was stirred under an Ar atmosphere at 0° C. for 8hours. After that, the mixture was left to stand at room temperatureovernight. After the completion of the reaction, the resultant wasneutralized with a saturated aqueous solution of NaHCO₃. The resultantsample was transferred to a separating funnel, and was extracted withCH₂Cl₂. The resultant sample was purified by column chromatography,whereby a white solid was obtained in an amount of 24.1 g in 80% yield.

FD-MS C₁₈H₁₀Br₂F₂O₂: theoretical value 456, observed value 456

(4) Synthesis of Compound 23

Compound 22 (24.1 g, 52.8 mmol), K₂CO₃ (16.0 g, 116 mmol), and NMP (220mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at 150° C. for 8 hours. After the completion ofthe reaction, the resultant was cooled to room temperature. Theresultant sample was transferred to a separating funnel, and water (500mL) was charged into the funnel. Then, the mixture was extracted withAcOEt. The resultant sample was purified by column chromatography,whereby a white solid was obtained in an amount of 18.7 g in 85% yield.

FD-MS C₁₈H₈Br₂O₂: theoretical value 416, observed value 416

(5) Synthesis of Compound No. 154

Compound 23 (2.5 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 154) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 0.9 g in20% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 12 (Synthesis of Compound No. 157)

(1) Synthesis of Compound 24

Compound 23 (16.8 g, 40.0 mmol), phenylboronic acid (4.8 g, 40 mmol), a2 M aqueous solution of Na₂CO₃ (80 mL, 160 mmol), DME (80 mL), toluene(80 mL), and Pd[PPh₃]₄ (2.3 g, 2.0 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (150 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 9.1 g in 55% yield.

FD-MS C₂₄H₁₃BrO₂: theoretical value 413, observed value 413

(2) Synthesis of Compound 25

Compound 24 (9.0 g, 21.8 mmol) and THF (220 mL) were loaded into athree-necked flask, and the mixture was cooled to −78° C. Then, n-BuLi(1.65 M solution in n-hexane, 14.5 mL, 23.9 mmol) was added dropwise tothe flask, and the resultant mixture was stirred at −78° C. for 20minutes. Triisopropyl borate (12.3 g, 65.3 mmol) was added to theresultant, and the mixture was stirred at −78° C. for 1 hour. Afterthat, the resultant was left to stand overnight at room temperature.Then, 1 N HCl (100 mL) was charged into the resultant, and the mixturewas stirred at room temperature for 1 hour. The resultant sample wasconcentrated, and was then transferred to a separating funnel. Water(100 mL) was charged into the funnel, and the mixture was extracted withCH₂Cl₂. The extract was dried with MgSO₄, and was then filtrated andconcentrated. The resultant sample was purified by recrystallization(toluene-hexane), whereby a white solid was obtained in an amount of 4.1g in 50% yield.

(3) Synthesis of Compound No. 157

Compound 25 (4.0 g, 10.6 mmol), 1,3-dibromobenzene (1.2 g, 5.3 mmol), a2 M aqueous solution of Na₂CO₃ (11 mL, 22 mmol), DME (11 mL), toluene(11 mL), and Pd[PPh₃]₄ (0.31 g, 0.27 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 157) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 0.63 gin 16% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 13 (Synthesis of Compound No. 239)

Compound 26 (2.8 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 239) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.1 g in45% yield.

FD-MS C₆₀H₄₂O₂: theoretical value 794, observed value 794

Synthesis Example 14 (Synthesis of Compound No. 249)

Compound 27 (2.8 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 249) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.5 g in52% yield.

FD-MS C₆₀H₄₂O₂: theoretical value 794, observed value 794

Synthesis Example 15 (Synthesis of Compound No. 259)

Compound 28 (2.8 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 259) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.9 g in40% yield.

FD-MS C₆₀H₄₂O₂: theoretical value 794, observed value 794

Synthesis Example 16 (Synthesis of Compound No. 269)

Compound 29 (2.8 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 269) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.0 g in21% yield.

FD-MS C₆₀H₄₂O₂: theoretical value 794, observed value 794

Synthesis Example 17 (Synthesis of Compound No. 233)

Compound 30 (2.7 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 233) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.9 g in40% yield.

FD-MS C₅₄H₃₀O₂S₂: theoretical value 774, observed value 774

Synthesis Example 18 (Synthesis of Compound No. 243)

Compound 31 (2.7 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 243) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.1 g in45% yield.

FD-MS C₅₄H₃₀O₂S₂: theoretical value 774, observed value 774

Synthesis Example 19 (Synthesis of Compound No. 253)

Compound 32 (2.7 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 253) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.8 g in38% yield.

FD-MS C₅₄H₃₀O₂S₂: theoretical value 774, observed value 774

Synthesis Example 20 (Synthesis of Compound No. 263)

Compound 33 (2.7 g, 6.0 mmol), Compound 9 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 263) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 0.6 g in13% yield.

FD-MS C₅₄H₃₀O₂S₂: theoretical value 774, observed value 774

Synthesis Example 21 (Synthesis of Compound No. 272)

Compound 11 (8.3 g, 21.9 mmol), 1,3,5-tribromobenzene (2.3 g, 7.3 mmol),a 2 M aqueous solution of Na₂CO₃ (22.5 mL, 45 mmol), DME (15 mL),toluene (15 mL), and Pd[PPh₃]₄ (0.63 g, 0.56 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 272) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.0 g in13% yield.

FD-MS C₇₈H₄₂O₆: theoretical value 1,075, observed value 1,075

Synthesis Example 22 (Synthesis of Compound No. 273)

Compound 17 (8.3 g, 21.9 mmol), 1,3,5-tribromobenzene (2.3 g, 7.3 mmol),a 2 M aqueous solution of Na₂CO₃ (22.5 mL, 45 mmol), DME (15 mL),toluene (15 mL), and Pd[PPh₃]₄ (0.63 g, 0.56 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 273) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.2 g in15% yield.

FD-MS C₇₈H₄206: theoretical value 1,075, observed value 1,075

Synthesis Example 23 (Synthesis of Compound No. 274)

Compound 19 (8.3 g, 21.9 mmol), 1,3,5-tribromobenzene (2.3 g, 7.3 mmol),a 2 M aqueous solution of Na₂CO₃ (22.5 mL, 45 mmol), DME (15 mL),toluene (15 mL), and Pd[PPh₃]₄ (0.63 g, 0.56 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 274) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 0.94 gin 12% yield.

FD-MS C₇₈H₄₂O₆: theoretical value 1,075, observed value 1,075

Synthesis Example 24 (Synthesis of Compound No. 276)

Compound 25 (8.3 g, 21.9 mmol), 1,3,5-tribromobenzene (2.3 g, 7.3 mmol),a 2 M aqueous solution of Na₂CO₃ (22.5 mL, 45 mmol), DME (15 mL),toluene (15 mL), and Pd[PPh₃]₄ (0.63 g, 0.56 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 276) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 0.55 gin 7% yield.

FD-MS C₇₈H₄₂O₆: theoretical value 1,075, observed value 1,075

Synthesis Example 25 (Synthesis of Compound No. 1)

Compound 8 (2.5 g, 6.0 mmol), compound 34 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 1) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.2 g in27% yield.

FD-MS C₅₄H₃₂N₂O₂: theoretical value 740, observed value 740

Synthesis Example 26 (Synthesis of Compound No. 92)

Compound 8 (2.5 g, 6.0 mmol), 3-biphenylboronic acid (2.6 g, 13.2 mmol),a 2 M aqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene(12 mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 92) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.1 g in32% yield.

FD-MS C₄₂H₂₆O₂: theoretical value 562, observed value 562

Synthesis Example 27 (Synthesis of Compound No. 108)

(1) Synthesis of Compound 35

4-bromofluorobenzene (81.55 g, 466 mmol), 3-biphenylboronic acid (92.33g, 466 mmol), a 2 M aqueous solution of Na₂CO₃ (530 mL), Pd[PPh₃]₄ (14.7g, 12.7 mmol), EWE (500 mL), and toluene (500 mL) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 6 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (350 mL) was charged into the funnel. Then, themixture was extracted with toluene. The extract was dried with MgSO₄,and was then filtrated and concentrated. The resultant sample waspurified by silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized, whereby awhite solid was obtained in an amount of 31.7 g in 27% yield.

FD-MS C₁₈H₁₃F: theoretical value 248, observed value 248

(2) Synthesis of Compound 36

Compound 35 (31.7 g, 127 mmol) and THF (200 mL) were loaded into athree-necked flask, and the mixture was cooled to −78° C. Then, lithium2,2,6,6-tetramethyl piperidine solution preliminarily prepared fromn-BuLi (1.55 M solution in hexane, 82 mL, 127 mmol), 2,2,6,6-tetramethylpiperidine (17.9 g, 127 mmol), and THF (50 mL) were added to the flask,and the resultant mixture was stirred at −78° C. under an Ar atmospherefor 2 hours. After that, triisopropyl borate (71.6 g, 381 mmol) wasadded to the mixture, followed by stirring at −78° C. for 2 hours. Then,the temperature of the obtained mixture was returned to room temperatureslowly and the mixture was left to stand overnight.

After the completion of the reaction, methanol (50 mL) was added toinactivate the resultant, and the resultant was concentrated to aboutthe half volume. CH₂Cl₂ (200 mL) and 2 N HCl (120 mL) were added,followed by stirring at room temperature for 2 hours. The resultantsample was transferred to a separating funnel, and extracted withCH₂Cl₂. The extract was dried with MgSO₄, and was then purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then subjected to dispersion washing withtoluene, whereby a white solid was obtained in an amount of 27.5 g in74% yield.

(3) Synthesis of Compound 37

1,3-dibromo-4,6-dimethoxybenzene (5.92 g, 20 mmol), Compound 36 (14.02g, 48 mmol), a 2 M aqueous solution of Na₂CO₃ (40 mL), Pd[PPh₃]₄ (1.15g, 1 mmol), DME (20 mL), and toluene (20 mL) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 36 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (100 mL) was charged into the funnel. Then, themixture was extracted with toluene. The extract was dried with MgSO₄,and was then filtrated and concentrated. The resultant sample waspurified by silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized, whereby awhite solid was obtained in an amount of 9.49 g in 75% yield.

FD-MS C₄₄H₃₂F₂O₂: theoretical value 630, observed value 630

(4) Synthesis of Compound 38

Compound 37 (9.49 g, 5 mmol) and CH₂Cl₂ (75 mL) were loaded into athree-necked flask, and the mixture was cooled to 0° C. Then, BBr₃(15.03 g, 60 mmol) was added to the flask, and the resultant mixture wasstirred under an Ar atmosphere at room temperature for 24 hours.

After the completion of the reaction, the obtained solution was cooledto −78° C., and inactivated using methanol (50 mL) and water (100 mL).The sample was transferred to a separating funnel, and water (100 mL)was charged into the funnel. Then, the mixture was extracted withCH₂Cl₂. The extract was dried with MgSO₄, and was then filtered andconcentrated. The obtained sample was purified by silica gel columnchromatography. The purified product was concentrated and exsiccated,whereby a white solid was obtained in an amount of 9.04 g in 100% yield.

FD-MS C₄₂H₂₈F₂O₂: theoretical value 602, observed value 602

(5) Synthesis of Compound No. 108

Compound 38 (9.04 g, 15 mmol) and NMP (150 mL) were loaded into athree-necked flask, and Compound 38 was dissolved completely. K₂CO₃(8.30 g, 60 mmol) was added to the flask, followed by stirring at 200°C. for 2 hours.

After the completion of the reaction, the obtained solution was cooledto room temperature. Toluene (1.5 L) was added to the resultant sample,and the sample was transferred to a separating funnel and washed withwater. The resultant was dried with MgSO₄ and then filtered andconcentrated. The resultant sample was purified by silica gel columnchromatography. The purified product was concentrated and exsiccated,and was then recrystallized, whereby a white powder (Compound No. 108)was obtained. The powder was purified by sublimation, whereby a whitesolid was obtained in an amount of 3.37 g in 40% yield.

FD-MS C₄₂H₂₆O₂: theoretical value 562, observed value 562

Synthesis Example 28 (Synthesis of Compound No. 281)

(1) Synthesis of Compound 39

1,3-dibromo-4,6-dimethoxybenzene (88.8 g, 300 mmol), 2-fluorophenylboric acid (100.7 g, 720 mmol), 2 M aqueous solution of Na₂CO₃ (600 mL),Pd[PPh₃]₄ (6.73 g, 6 mmol), DME (150 mL), and toluene (150 mL) wereloaded into a three-necked flask, and the mixture was refluxed under anAr atmosphere for 36 hours.

After the completion of the reaction, the obtained solution was cooledto room temperature. The resultant sample was transferred to aseparating funnel, and water (500 mL) was charged into the funnel. Then,the mixture was extracted with toluene. After being dried with MgSO₄,the extract was filtered and concentrated. The resultant sample waspurified by silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized, whereby awhite solid was obtained in an amount of 86.5 g in 88% yield.

FD-MS C₂₀H₁₆F₂O₂: theoretical value 326, observed value 326

(2) Synthesis of Compound 40

Compound 39 (48.3 g, 148 mmol) and CH₂Cl₂ (740 mL) were loaded into athree-necked flask, and the mixture was cooled to 0° C. Then, BBr₃ (89.0g, 355 mmol) was added to the flask, and the resultant mixture wasstirred at room temperature for 24 hours.

After the completion of the reaction, the obtained solution was cooledto −78° C., and inactivated using methanol (50 mL) and water (100 mL).The sample was transferred to a separating funnel. Then, the mixture wasextracted with CH₂Cl₂. The extract was dried with MgSO₄, and was thenfiltered and concentrated. The obtained sample was purified by silicagel column chromatography. The purified product was concentrated andexsiccated, whereby a white solid was obtained in an amount of 44.14 gin 100% yield.

FD-MS C₁₈H₁₂F₂O₂: theoretical value 298, observed value 298

(3) Synthesis of Compound 41

Compound 40 (44.14 g, 148 mmol) and NMP (888 mL) were loaded into athree-necked flask, and Compound 40 was dissolved completely. K₂CO₃(81.8 g, 592 mmol) was added to the flask, followed by stirring at 200°C. for 2 hours.

After the completion of the reaction, the obtained solution was cooledto room temperature. The sample was transferred to a separating funnel,toluene (2 L) was added, and the resultant was a washed with water. Theresultant was dried with MgSO₄ and then filtered and concentrated. Theresultant sample was purified by silica gel column chromatography. Thepurified product was concentrated and exsiccated, and was thenrecrystallized, whereby a white solid was obtained in an amount of 27.9g in 73% yield.

FD-MS C₁₈H₁₀O₂: theoretical value 258, observed value 258

(4) Synthesis of Compound 42

Compound 41 (12.9 g, 50 mmol) and THF (300 mL) were loaded into athree-necked flask, and the mixture was cooled to −78° C. Then, n-BuLi(2.63 M solution in hexane, 20.0 mL, 52.5 mmol) was added to the flask,and the resultant mixture was stirred at room temperature under an Aratmosphere for 1 hour. Next, the resultant was cooled to −78° C. again,trimethyl borate (10.4 g, 100 mmol) was added to the resultant. Afterbeing stirred at −78° C. for 10 minutes, the mixture was stirred at roomtemperature for 1 hour. After the completion of the reaction, theresultant was concentrated to about the half volume. 1 N HCl (200 mL)was added to the concentrated resultant, followed by stirring at roomtemperature for 1 hour. The resultant sample was transferred to aseparating funnel, and the mixture was extracted with ethyl acetate.After being dried with MgSO₄, the extract was concentrated. Theconcentrated product was subjected to dispersion washing with atoluene/hexane mixed solvent, whereby a white solid was obtained in anamount of 13.7 g in 91% yield.

(5) Synthesis of Compound No. 281

Compound 42 (3.8 g, 12.6 mmol), 1,3-dibromobenzene (1.4 g, 6.0 mmol), a2 M aqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene(12 mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 281) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.3 g in37% yield.

FD-MS C₄₂H₂₂O₄: theoretical value 590, observed value 590

Synthesis Example 29 (Synthesis of Compound No. 284)

(1) Synthesis of Compound 43

Compound 41 (2.69 g, 10.4 mmol) and THF (62 mL) were loaded into athree-necked flask, and the mixture was cooled to −78° C. Then, n-BuLi(1.66 M solution in hexane, 6.6 mL, 10.9 mmol) was added to the flask,and the resultant mixture was stirred at room temperature for 30minutes. Next, the resultant was cooled to −78° C. again, I₂ (2.69 g,10.6 mmol) was added to the resultant. After being stirred at −78° C.for 10 minutes, the mixture was stirred at room temperature for 1 hour.

After the completion of the reaction, water (30 mL) was added toinactivate the obtained solution, followed by concentration. After beingsubjected to dispersion washing with water, the sample was collected byfiltration and then dissolved in toluene. After being dried with MgSo₄,the resultant was filtered and concentrated. The obtained sample waspurified by silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized, whereby awhite solid was obtained in an amount of 3.77 g in 94% yield.

FD-MS C₁₈H₉IO₂: theoretical value 384, observed value 384

(2) Synthesis of Compound No. 284

Compound 43 (2.3 g, 6.0 mmol), Compound 44 (2.2 g, 6.3 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.30 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 284) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.0 g in30% yield.

FD-MS C₄₀H₂₄N₂O₂: theoretical value 564, observed value 564

Synthesis Example 30 (Synthesis of Compound No. 306)

(1) Synthesis of Compound 46

1,2-difluoro-3,6-diiodobenzene (7.3 g, 20.0 mmol), Compound 45 (12.8 g,42.0 mmol), a 2 M aqueous solution of Na₂CO₃ (40 mL, 80.0 mmol), DME (40mL), toluene (40 mL), and Pd[PPh₃]₄ (1.2 g, 1.0 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (100 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 8.2 g in 65% yield.

FD-MS C₄₄H₃₂F₂O₂: theoretical value 630, observed value 630

(2) Synthesis of Compound 47

Compound 46 (8.2 g, 13.0 mmol), a 1 M solution of BBr₃ in CH₂Cl₂ (32 mL,32.0 mmol), and CH₂Cl₂ (100 mL) were loaded into a three-necked flask,and the mixture was stirred under an Ar atmosphere at 0° C. for 8 hours.After that, the mixture was left to stand at room temperature overnight.

After the completion of the reaction, the resultant was neutralized witha saturated aqueous solution of NaHCO₃. The resultant sample wastransferred to a separating funnel, and was extracted with CH₂Cl₂. Theresultant sample was purified by silica gel column chromatography,whereby a white solid was obtained in an amount of 7.6 g in 97% yield.

FD-MS C₄₂H₂₈F₂O₂: theoretical value 602, observed value 602

(3) Synthesis of Compound No. 306

Compound 47 (7.6 g, 12.6 mmol), K₂CO₃ (7.0 g, 50.4 mmol), and NMP (50mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at 200° C. for 3 hours. After the completion ofthe reaction, the resultant was cooled to room temperature. Toluene (500mL) was charged into the resultant sample. The mixture was transferredto a separating funnel, and was washed with water. The washed productwas dried with MgSO₄, and was then filtrated and concentrated. Theresultant sample was purified by silica gel column chromatography. Thepurified product was concentrated and exsiccated, and was thenrecrystallized twice, whereby a white powder (Compound No. 306) wasobtained. The powder was purified by sublimation, whereby a white solidwas obtained in an amount of 2.9 g in 41% yield.

FD-MS C₄₂H₂₆O₂: theoretical value 562, observed value 562

Synthesis Example 31 (Synthesis of Compound No. 329)

(1) Synthesis of Compound 48

1,3-dibromo-4,6-difluorobenzene (5.4 g, 20.0 mmol), Compound 45 (12.8 g,42.0 mmol), a 2 M aqueous solution of Na₂CO₃ (40 mL, 80.0 mmol), DME (40mL), toluene (40 mL), and Pd[PPh₃]₄ (1.2 g, 1.0 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (100 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 7.2 g in 57% yield.

FD-MS C₄₄H₃₂F₂O₂: theoretical value 630, observed value 630

(2) Synthesis of Compound 49

Compound 46 (7.2 g, 11.4 mmol), a 1 M solution of BBr₃ in CH₂Cl₂ (28 mL,28.0 mmol), and CH₂Cl₂ (85 mL) were loaded into a three-necked flask,and the mixture was stirred under an Ar atmosphere at 0° C. for 8 hours.After that, the mixture was left to stand at room temperature overnight.

After the completion of the reaction, the resultant was neutralized witha saturated aqueous solution of NaHCO₃. The resultant sample wastransferred to a separating funnel, and was extracted with CH₂Cl₂. Theresultant sample was purified by silica gel column chromatography,whereby a white solid was obtained in an amount of 6.9 g in 100% yield.

FD-MS C₄₂H₂₈F₂O₂: theoretical value 602, observed value 602

(3) Synthesis of Compound No. 329

Compound 47 (6.9 g, 11.4 mmol), K₂CO₃ (6.3 g, 45.6 mmol), and NMP (50mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at 200° C. for 3 hours. After the completion ofthe reaction, the resultant was cooled to room temperature. Toluene (500mL) was charged into the resultant sample. The mixture was transferredto a separating funnel, and was washed with water. The washed productwas dried with MgSO₄, and was then filtrated and concentrated. Theresultant sample was purified by silica gel column chromatography. Thepurified product was concentrated and exsiccated, and was thenrecrystallized twice, whereby a white powder (Compound No. 329) wasobtained. The powder was purified by sublimation, whereby a white solidwas obtained in an amount of 2.3 g in 36% yield.

FD-MS C₄₂H₂₆O₂: theoretical value 562, observed value 562

An apparatus and measurement conditions adopted for field desorptionmass spectrometry (FD-MS) in each of Synthesis Examples 1 to 31 areshown below.

-   -   Apparatus: HX110 (manufactured by JEOL Ltd.)    -   Conditions: accelerating voltage 8 kV        -   scan range m/z=50 to 1,500        -   emitter kind: carbon        -   emitter current: 0 mA→2 mA/min→40 mA (held for 10 minutes)

Example 1

(Production of Organic EL Device)

A glass substrate provided with an ITO transparent electrode measuring25 mm by 75 mm by 1.1 mm (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes.Further, the substrate was subjected to ultraviolet (UV)-ozone cleaningfor 30 minutes.

The glass substrate provided with a transparent electrode thus cleanedwas mounted on a substrate holder of a vacuum deposition apparatus.First, Compound A was deposited from the vapor onto the surface of theglass substrate on the side where a transparent electrode line wasformed so as to cover the transparent electrode, whereby a holetransporting layer having a thickness of 30 nm was obtained.

Compound No. 11 as a host for phosphorescence and Ir(Ph-ppy)3 as adopant for phosphorescence were co-deposited from the vapor onto thehole transporting layer, whereby a phosphorescent layer having athickness of 30 nm was obtained. The concentration of Ir(Ph-ppy)₃ was 5mass %.

Subsequently, Compound B having a thickness of 10 nm, Compound C havinga thickness of 20 nm, LiF having a thickness of 1 nm, and metal Alhaving a thickness of 80 nm were sequentially laminated on thephosphorescent layer, whereby a cathode was obtained. It should be notedthat LiF as an electron injectable electrode was formed at a rate of 1Å/min.

(Evaluation of Organic EL Device for Light Emitting Performance)

The organic EL device thus produced was caused to emit light by beingdriven with a direct current. The luminance (L) of the emitted light andthe current density at which the device started to emit the light weremeasured. Then, the current efficiency (L/J) of the device at aluminance of 1,000 cd/m² was determined. Further, the lifetime of thedevice at a luminance of 20,000 cd/m² was determined. Table 1 shows theresults.

Examples 2 to 26

Organic EL devices were each produced in the same manner as in Example 1except that a host material listed in Table 1 was used instead of HostCompound No. 11 in Example 1, and the devices were each evaluated in thesame manner as in Example 1. Table 1 shows the results of the evaluationfor light emitting performance.

Comparative Examples 1 to 7

Organic EL devices were each produced in the same manner as in Example 1except that the following compounds (a) to (g) described in EP 0908787 Awas used as a host material instead of Host Compound No. 11 in Example1, and the devices were each evaluated in the same manner as inExample 1. Table 1 shows the results of the evaluation for lightemitting performance.

Comparative Examples 8 to 11

Organic EL devices were each produced in the same manner as in Example 1except that the following compounds (h) to (k) described in WO2006-122630 was used as a host material instead of Host Compound No. 11in Example 1, and the devices were each evaluated in the same manner asin Example 1. Table 1 shows the results of the evaluation for lightemitting performance.

Comparative Examples 12 and 13

An organic EL device was produced in the same manner as in Example 1except that the following compound (1) or (m) described in WO2007-063754 was used as a host material instead of Host Compound No. 11in Example 1, and the device was evaluated in the same manner as inExample 1. Table 1 shows the results of the evaluation for lightemitting performance.

Comparative Example 14

An organic EL device was produced in the same manner as in Example 1except that the following compound (n) described in US 2002-0132134 Aand US 2003-0044646 A was used as a host material instead of HostCompound No. 11 in Example 1, and the device was evaluated in the samemanner as in Example 1. Table 1 shows the results of the evaluation forlight emitting performance.

Comparative Example 15

An organic EL device was produced in the same manner as in Example 1except that the following compound (o) described in JP 2008-81494 A wasused as a host material instead of Host Compound No. 11 in Example 1,and the device was evaluated in the same manner as in Example 1. Table 1shows the results of the evaluation for light emitting performance.

TABLE 1 Voltage Efficiency Life time Host (V) (cd/A) (hr) com- @ 20 @1,000 @ 20,000 pound mA/cm² cd/m² cd/m² Example 1 (11) 5.3 47.6 190Example 2 (40) 5.2 46.2 200 Example 3 (47) 5.3 47.1 200 Example 4 (66)5.4 49.1 160 Example 5 (100) 5.5 58.2 250 Example 6 (103) 5.6 59.1 230Example 7 (116) 5.5 58.3 300 Example 8 (119) 5.5 57.1 320 Example 9(134) 5.2 54.9 290 Example 10 (139) 5.3 55.3 280 Example 11 (154) 5.559.3 200 Example 12 (157) 5.6 60.1 180 Example 13 (233) 5.3 54.3 150Example 14 (239) 5.5 58.5 420 Example 15 (243) 5.5 55.9 90 Example 16(249) 5.6 58.3 440 Example 17 (253) 5.6 56.6 80 Example 18 (259) 5.859.7 400 Example 19 (263) 5.7 57.2 70 Example 20 (269) 5.9 59.8 360Example 21 (272) 5.5 55.7 420 Example 22 (273) 5.4 55.8 470 Example 23(274) 5.4 59.7 410 Example 24 (276) 5.6 59.9 250 Example 25 (1) 5.4 54.3510 Example 26 (108) 6.1 58.7 530 Comparative Example 1 (a) 4.6 26.5 50Comparative Example 2 (b) 4.7 28.9 60 Comparative Example 3 (c) 4.5 23.150 Comparative Example 4 (d) 4.7 28.1 60 Comparative Example 5 (e) 4.726.1 30 Comparative Example 6 (f) 4.2 17.6 30 Comparative Example 7 (g)4.3 18.5 30 Comparative Example 8 (h) 4.9 37.5 50 Comparative Example 9(i) 4.7 35.9 60 Comparative Example 10 (j) 4.7 55.5 50 ComparativeExample 11 (k) 4.5 35.7 50 Comparative Example 12 (l) 4.3 17.3 30Comparative Example 13 (m) 4.5 17.7 20 Comparative Example 14 (n) 5.428.7 60 Comparative Example 15 (o) 5.5 38.2 50

Example 27

(Production of Organic EL Device)

The glass substrate provided with a transparent electrode cleaned in thesame manner as described above was mounted on a substrate holder of avacuum deposition apparatus. First, Compound A was deposited from thevapor onto the surface of the glass substrate on the side where atransparent electrode line was formed so as to cover the transparentelectrode, whereby a hole transporting layer having a thickness of 30 nmwas obtained.

Compound No. 108 as a host for phosphorescence and Ir(Ph-ppy) 3 as adopant for phosphorescence were co-deposited from the vapor onto thehole transporting layer, whereby a phosphorescent layer having athickness of 30 nm was obtained. The concentration of Ir(Ph-ppy)₃ was 10mass %.

Subsequently, Compound No. 92 having a thickness of 10 nm, Compound Chaving a thickness of 20 nm, LiF having a thickness of 1 nm, and metalAl having a thickness of 80 nm were sequentially laminated on thephosphorescent layer, whereby a cathode was obtained. It should be notedthat LiF as an electron injectable electrode was formed at a rate of 1Å/min.

(Evaluation of Organic EL Device for Light Emitting Performance)

The organic EL device thus produced was caused to emit light by beingdriven with a direct current. The luminance (L) of the emitted light andthe current density at which the device started to emit the light weremeasured. Then, the current efficiency (L/J) of the device at aluminance of 1,000 cd/m² was determined. Further, the lifetime of thedevice at a luminance of 20,000 cd/m² was determined. Table 2 shows theresults.

Examples 28 to 37

Organic EL devices were each produced in the same manner as in Example27 except that a host compound and an electron transportable compoundlisted in Table 2 were used instead of Host Compound No. 108 andElectron Transportable Compound No. 92 in Example 27, and the deviceswere each evaluated in the same manner as in Example 27. Table 2 showsthe results of the evaluation for light emitting performance.

Comparative Example 16

An organic EL device was produced in the same manner as in Example 27except that: CBP was used instead of Host Compound No. 108 in Example27; and BAlq was used instead of Electron Transportable Compound No. 92in Example 27. Then, the device was evaluated in the same manner as inExample 27. Table 2 shows the results of the evaluation for lightemitting performance.

TABLE 2 Electron Voltage Efficiency Life time Host trans- (V) (cd/A)(hr) com- portable @ 20 @ 1,000 @ 20,000 pound compound mA/cm² cd/m²cd/m² Example 27 (108) (92) 5.8 60.2 580 Example 28 (108) (306) 5.7 62.1560 Example 29 (108) (108) 6.0 63.7 600 Example 30 (108) (329) 5.9 62.3550 Example 31 (1) (92) 4.8 55.6 550 Example 32 (103) (92) 5.5 66.1 590Example 33 (119) (92) 5.7 68.9 570 Example 34 CBP (92) 5.7 48.5 100Example 35 CBP (306) 5.6 49.6 120 Example 36 CBP (108) 5.9 48.2 100Example 37 CBP (329) 5.8 49.3 120 Compaiative CBP BAlq 6.5 45.1 30Example 16

Each of the organic EL devices of the comparative examples showed alower current efficiency, was driven at a higher voltage, and had ashorter lifetime than those of each of the organic EL devices of theexamples.

INDUSTRIAL APPLICABILITY

As described above in detail, the utilization of the material for anorganic EL device of the present invention can provide an organic ELdevice which shows high luminous efficiency, is free of any pixeldefect, and has a long lifetime. Accordingly, the organic EL device ofthe present invention is extremely useful as, for example, a lightsource for various electronic instruments. In addition, the material canbe effectively used also as a material for an organic electron device,and is extremely useful in an organic solar cell, organic semiconductorlaser, a sensor using organic matter, or an organic TFT.

1. (canceled)
 2. A material for an organic electroluminescence devicerepresented by any one of formulas (5) to (14):

wherein formulas (5) and (6): one of X₅ and X₆ is S and the other of X₅and X₆ is O, S, or CR₂R₃; R₂, and R₃ each independently represent analkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, anaralkyl group having 7 to 24 carbon atoms, a silyl group having 3 to 20carbon atoms, a substituted or unsubstituted aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted aromatic heterocyclic group having a ring formed of 3 to24 atoms; n represents 2, 3, or 4, and the material represented by theformula (6) comprises a dimer using L₃ as a linking group for n=2, atrimer using L₃ as a linking group for n=3, or a tetramer using L₃ as alinking group for n=4; L₁ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond; L₂ representsa single bond, an alkyl or alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl or cycloalkylene group having aring formed of 3 to 20 carbon atoms, a monovalent or divalent silylgroup having 2 to 20 carbon atoms, a substituted or unsubstituted,monovalent or divalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalentor divalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with a benzene ring c through acarbon-carbon bond; when n represents 2, L₃ represents a single bond, analkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond; A₁ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withL₁ through a carbon-carbon bond, provided that, when L₁ represents analkyl or alkylene group having 1 to 20 carbon atoms, a case where A₁represents a hydrogen atom is excluded; A₂ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstitutedaromatic heterocyclic group which has a ring formed of 3 to 24 atoms andwhich is linked with L₂ through a carbon-carbon bond, provided that,when represents an alkyl or alkylene group having 1 to 20 carbon atoms,a case where A₂ represents a hydrogen atom is excluded; Y₁, Y₂, and Y₃each represent an alkyl group having 1 to 20 carbon atoms, a substitutedor unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an alkoxy group having 1 to 20 carbon atoms, an aralkyl grouphaving 7 to 24 carbon atoms, a silyl group having 3 to 20 carbon atoms,a substituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstitutedaromatic heterocyclic group which has a ring formed of 3 to 24 atoms andwhich is linked with the benzene ring a, b, or c through a carbon-carbonbond, a number of each of Y₁, Y₂, and Y₃ is 0, 1,2, or 3, and a numberof Y₂ is 0, 1, or 2; and A₁, A₂, L₁, L₂, and L₃ are each free of anycarbonyl group; wherein formulas (7) to (12): one of X₇ and X₈ is S andthe other of X₇ and X₈ is O, S, or CR₂R₃, one of X₉ and X₁₀ is S and theother of X₉ and X₁₀ is O, S, or CR₂R₃, and one of X₁₁ and X₁₂ is S andthe other of X₁₁ and X₁₂ is O, S, or CR₂R₃; R₂, and R₃ eachindependently represent an alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, asilyl group having 3 to 20 carbon atoms, a substituted or unsubstitutedaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or substituted or unsubstituted aromatic heterocyclic group having aring formed of 3 to 24 atoms; n represents 2,3, or 4, and the materialrepresented by any one of the formulae (10) to (12) comprises a dimerusing L₃ as a linking group for n=2, a trimer using L₃ as a linkinggroup for n=3, or a tetramer using L₃ as a linking group for n=4; L₁represents a single bond, an alkyl or alkylene group having 1 to 20carbon atoms, a substituted or unsubstituted cycloalkyl or cycloalkylenegroup having a ring formed of 3 to 20 carbon atoms, a monovalent ordivalent silyl group having 2 to 20 carbon atoms, a substituted orunsubstituted, monovalent or divalent aromatic hydrocarbon group havinga ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, monovalent or divalent aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with a benzenering a through a carbon-carbon bond; L₂ represents a single bond, analkyl or alkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond; when nrepresents 2, L₃ represents a single bond, an alkylene group having 1 to20 carbon atoms, a substituted or unsubstituted cycloalkylene grouphaving a ring formed of 3 to 20 carbon atoms, a divalent silyl grouphaving 2 to 20 carbon atoms, a substituted or unsubstituted, divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, divalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond, when n represents 3, L₃represents a trivalent alkane having 1 to 20 carbon atoms, a substitutedor unsubstituted, trivalent cycloalkane having a ring formed of 3 to 20carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted, trivalent aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, trivalent aromatic heterocyclic group which has 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, or when n represents 4, L₃ represents a tetravalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, asilicon atom, a substituted or unsubstituted, tetravalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, tetravalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond; A₁ represents a hydrogenatom, a substituted or unsubstituted cycloalkyl group having a ringformed of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbonatoms, a substituted or unsubstituted aromatic hydrocarbon group havinga ring formed of 6 to 24 carbon atoms, or a substituted or unsubstitutedaromatic heterocyclic group which has a ring formed of 3 to 24 atoms andwhich is linked with L₁ through a carbon-carbon bond, provided that,when L_(t) represents an alkyl or alkylene group having 1 to 20 carbonatoms, a case where A₁ represents a hydrogen atom is excluded; A₂represents a hydrogen atom, a substituted or unsubstituted cycloalkylgroup having a ring formed of 3 to 20 carbon atoms, a silyl group having3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group which has aring formed of 3 to 24 atoms and which is linked with L₂ through acarbon-carbon bond, provided that, when L₂ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₂ represents ahydrogen atom is excluded; Y₁, Y₂, and Y₃ each represent an alkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylgroup having a ring formed of 3 to 20 carbon atoms, an alkoxy grouphaving 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, a number ofeach of Y₁, Y₂, and Y₃ is 0, 1, 2, or 3, and a number of Y₂ is 0, 1, or2; and A₁, A₂, L₁, L₂, and L₃ are each free of any carbonyl group;wherein formulas (13) and (14): one of X₁₃ and X₁₄ is S and the other ofX₁₃ and X₁₄ is O, S, or CR₂R₃; R₂, and R₃ each independently representan alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, orsubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms; n represents 2,3, or 4, and the materialrepresented by the formula (14) comprises a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4; L₁ represents a singlebond, an alkyl or alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl or cycloalkylene group having aring formed of 3 to 20 carbon atoms, a monovalent or divalent silylgroup having 2 to 20 carbon atoms, a substituted or unsubstituted,monovalent or divalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalentor divalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with a benzene ring a through acarbon-carbon bond; L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond; when nrepresents 2, L₃ represents a single bond, an alkylene group having 1 to20 carbon atoms, a substituted or unsubstituted cycloalkylene grouphaving a ring formed of 3 to 20 carbon atoms, a divalent silyl grouphaving 2 to 20 carbon atoms, a substituted or unsubstituted, divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, divalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond, when n represents 3, L₃represents a trivalent alkane having 1 to 20 carbon atoms, a substitutedor unsubstituted, trivalent cycloalkane having a ring formed of 3 to 20carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted, trivalent aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, trivalent aromatic heterocyclic group which has 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, or when n represents 4, L₃ represents a tetravalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, asilicon atom, a substituted or unsubstituted, tetravalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, tetravalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond; A₁ represents a hydrogenatom, a substituted or unsubstituted cycloalkyl group having a ringformed of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbonatoms, a substituted or unsubstituted aromatic hydrocarbon group havinga ring formed of 6 to 24 carbon atoms, or a substituted or unsubstitutedaromatic heterocyclic group which has a ring formed of 3 to 24 atoms andwhich is linked with L₁ through a carbon-carbon bond, provided that,when L_(t) represents an alkyl or alkylene group having 1 to 20 carbonatoms, a case where A₁ represents a hydrogen atom is excluded; A₂represents a hydrogen atom, a substituted or unsubstituted cycloalkylgroup having a ring formed of 3 to 20 carbon atoms, a silyl group having3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group which has aring formed of 3 to 24 atoms and which is linked with L₂ through acarbon-carbon bond, provided that, when L₂ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₂ represents ahydrogen atom is excluded; Y₁, Y₂, and Y₃ each represent an alkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylgroup having a ring formed of 3 to 20 carbon atoms, an alkoxy grouphaving 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, a number ofeach of Y₁ and Y₃ is 0, 1,2, or 3, and a number of Y₂ is 0, 1, or 2; andA₁, A₂, L₁, L₂, and L₃ are each free of any carbonyl group.
 3. Thematerial for an organic electroluminescence device according to claim 2,which is represented by one of formulae (5) and (6).
 4. The material foran organic electroluminescence device according to claim 2, wherein thematerial for an organic electroluminescence device is represented by anyone of the formulae (7) to (12).
 5. The material for an organicelectroluminescence device according to claim 2, wherein the material isrepresented by one of formulae (13) and (14).
 6. The material for anorganic electroluminescence device according to claim 2, wherein thematerial is represented by formula (6) wherein n represents
 2. 7. Thematerial for an organic electroluminescence device according to claim 2,wherein the material is represented by any one of formulas (10) to (12)wherein n represents
 2. 8. The material for an organicelectroluminescence device according to claim 2, wherein the material isrepresented by formula (14) wherein n represents
 2. 9. The material foran organic electroluminescence device according to claim 2, wherein thematerial is represented by formulas (5) or (6) wherein a total number ofsubstituents represented by Y₁, Y₂, and Y₃ in the general formula (5) is3 or less, and a total number of the substituents represented by Y₁, Y₂,and Y₃ in the structure of [ ]_(n) in the general formula (6) is 3 orless.
 10. The material for an organic electroluminescence deviceaccording to claim 2, wherein the material is represented by any one offormulas (7) to (12) wherein a total number of substituents representedby Y₁, Y₂, and Y₃ in the general formulae (7) to (9) is 3 or less, and atotal number of the substituents represented by Y₁, Y₂, and Y₃ in thestructure of [ ]_(n) in the general formulae (10) to (12) is 3 or less.11. The material for an organic electroluminescence device according toclaim 2, wherein the material is represented by formulas (13) or (14)wherein a total number of substituents represented by Y₁, Y₂, and Y₃ inthe general formula (13) is 3 or less, and a total number of thesubstituents represented by Y₁, Y₂, and Y₃ in the structure of [ ]_(n)in the general formula (14) is 3 or less.
 12. An organicelectroluminescence device comprising one or more organic thin filmlayers including a light emitting layer between a cathode and an anode,wherein at least one layer of the organic thin film layers contains thematerial for an organic electroluminescence device according to claim 2as a compound having a π-conjugated heteroacene skeleton crosslinkedwith a carbon atom, oxygen atom, or sulfur atom.
 13. The organicelectroluminescence device according to claim 12, wherein the lightemitting layer contains the material for an organic electroluminescencedevice as a host material.
 14. The organic electroluminescence deviceaccording to claim 13, wherein the light emitting layer further containsa phosphorescent material.
 15. The organic electroluminescence deviceaccording to claim 12, wherein the light emitting layer contains a hostmaterial and a phosphorescent material, and the phosphorescent materialcomprises an orthometalated complex of an iridium (Ir), osmium (Os), orplatinum (Pt) metal.
 16. The organic electroluminescence deviceaccording to claim 12, further comprising an electron injecting layerbetween the light emitting layer and the cathode, wherein the electroninjecting layer contains a nitrogen-containing ring derivative.
 17. Theorganic electroluminescence device according to claim 12, furthercomprising an electron transporting layer between the light emittinglayer and the cathode, wherein the electron transporting layer containsthe material for an organic electroluminescence device.
 18. The organicelectroluminescence device according to claim 17, wherein the lightemitting layer contains the material for an organic electroluminescencedevice as a host material.
 19. The organic electroluminescence deviceaccording to claim 12, further comprising a hole transporting layerbetween the light emitting layer and the anode, wherein the holetransporting layer contains the material for an organicelectroluminescence device.
 20. The organic electroluminescence deviceaccording to claim 12, further comprising a reducing dopant at aninterfacial region between the cathode and the organic thin film layers.21. An organic electroluminescence device comprising one or more organicthin film layers including a light emitting layer between a cathode andan anode, wherein at least one layer of the organic thin film layerscontains the material for an organic electroluminescence devicerepresented by any one of formulae (5) and (6) according to claim 2 as acompound having a π-conjugated heteroacene skeleton crosslinked with acarbon atom, oxygen atom, or sulfur atom, wherein the organicelectroluminescence device further comprises an electron transportinglayer between the light emitting layer and the cathode, and wherein theelectron transporting layer contains the material for an organicelectroluminescence device as a host material.
 22. An organicelectroluminescence device comprising one or more organic thin filmlayers including a light emitting layer between a cathode and an anode,wherein at least one layer of the organic thin film layers contains thematerial for an organic electroluminescence device represented by anyone of formulae (9) and (12) according to claim 2 as a compound having aπ-conjugated heteroacene skeleton crosslinked with a carbon atom, oxygenatom, or sulfur atom, wherein the organic electroluminescence devicefurther comprises an electron transporting layer between the lightemitting layer and the cathode, and wherein the electron transportinglayer contains the material for an organic electroluminescence device asa host material.
 23. An organic electroluminescence device comprisingone or more organic thin film layers including a light emitting layerbetween a cathode and an anode, wherein at least one layer of theorganic thin film layers contains the material for an organicelectroluminescence device according to claim 2 as a compound having aπ-conjugated heteroacene skeleton crosslinked with a carbon atom, oxygenatom, or sulfur atom.
 24. The organic electroluminescence deviceaccording to claim 23, wherein the light emitting layer contains thematerial for an organic electroluminescence device as a host material.25. The organic electroluminescence device according to claim 24,wherein the light emitting layer further contains a phosphorescentmaterial.